


You Think You're Tough

by volantcas, vulcancas



Category: Supernatural
Genre: 10 Things I Hate About You AU, Alternate Universe - High School, Fake/Pretend Relationship, Homophobic Language, M/M, Romantic Comedy, Swearing, Underage Drinking
Language: English
Status: Completed
Published: 2017-11-21
Updated: 2017-11-21
Packaged: 2019-02-05 01:00:40
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 35,921
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12783504
Author URL: https://archiveofourown.org/users/volantcas/pseuds/volantcas, https://archiveofourown.org/users/vulcancas/pseuds/vulcancas
Summary: Mere months from graduating, Castiel Novak is desperate to escape Seattle. Life in the Emerald City can be unbearable for someone subjected to the torment of Robert Thompson High School and its vapid students, among them Castiel’s social sell-out younger sister Jessica Moore and the conceited Tyson Brady. Cas and his only friend, Gilda, have navigated Thompson’s tedium as Out and Proud™ social outcasts. Too busy reading queer manifestos, saving the bees, and battling the Patriarchy one English paper at a time, his foster mom Sheriff Jody Mills’ strict no dating policy has never bothered Cas. Everything changes when Sam Winchester returns to Seattle for a fresh start, promising himself to keep his nose down and salvage his relationship with his older brother Dean. That is, until he catches sight of the lovely Jess. Sam enlists the help of his new friend Charlie and the two of them concoct a dubious plan. First: find someone who can convince the hostile Castiel Novak to go on a date with him, someone like Dean, who isn’t even on speaking terms with Sam. Then, trick someone flush with cash but low on brains into sponsoring their little scheme - someone like Tyson Brady, who also happens to want Jess for himself. Simple, right?





	1. ACT I

**Author's Note:**

> Well it's finally here! What started as a series of texts discussing how great it would be if a 10 Things I Hate About You AU existed while we were bored during class is now an actual 30k+ big bang! We're really excited to be sharing this with everyone especially since it's our first Big Bang (and deancas fic!)! Just a disclaimer, we don't own anything from spn or 10 things! 
> 
> A big thank you to our artist koisocks who made AMAZING art for this fic, which you can see [HERE.](http://koisocks.tumblr.com/post/167756109511/you-think-youre-tough-written-by-preciousmish)
> 
> Another round of thank yous to our lovely beta [Thrisha](http://www.deanwinchcester.tumblr.com)(any mistakes you see are on us for adding things) and of course, the dcbb mods Muse and Jojo. 
> 
> So without further ado, here's the fic!

“Here. Comes. Trouble.” 

Billie’s fingers tensed on the steering wheel as she watched the Continental approach in her rear-view mirror while she sat stopped at the red light, her friends growing silent at her announcement. The peppy pop song playing in the convertible was gradually drowned out by deafening rock pounding from the Continental’s ancient speakers, which shook the surrounding pavement. Sitting beside Billie in the passenger seat, Jessica Moore clapped her hands to her ears to muffle the roar, leaning forward to glare around Billie at the driver that had pulled up beside them. The offending vehicle's brakes groaned as it lurched to a stop.

Gaze concealed behind sunglasses, warranted for even the smallest glimpses of sun this time of year, Castiel looked straight ahead and strummed his fingers on the wheel, paying no heed to the daggers directed at him from the adjacent car except to reach out and dial the volume impossibly louder. His expression betrayed no notice of his speaker’s painful straining.

The traffic light flicked to green and Billie accelerated without sparing a glance at the other driver, leaving behind the ’78 Lincoln with perhaps more speed than was strictly necessary. Cas swung into the high school parking lot moments later and throngs of students hustled away at the sight of his approach. It was no different after he emerged from his car, backpack slung over one shoulder as he walked alone to the front entrance. Most people automatically sidestepped to avoid his path. He could feel their wary gazes landing on his back, but the routine didn’t faze him. What caught his attention instead was the newly tacked-up poster, which read _‘Robert Thompson High School Spring 2000 Formal._ ’ Cas knocked into a boy’s bag and viciously tore down the announcement, ignoring the boy’s annoyed “ _Hey_!” He crushed the poster into a ball, tossing it towards the recycling bin.

The bell rang just as he stepped inside the school entrance, his timing impeccable after years of the high school drill had effectively tuned his body to the school’s clocks. Footsteps grew more urgent as freshmen rushed to their morning periods. Cas, along with the other groggy upperclassmen, strolled less hastily. Once he arrived outside his English Lit classroom, he paused to see his teacher Mr. Henriksen writing on the chalkboard. 

An impatient breath in his ear. “Do you _mind_?” 

Cas turned and raised an eyebrow at the knot of classmates that had already formed behind him as he stood blocking the doorway. He scowled at them before stepping inside, letting his backpack thud loudly to the floor beside him as he dropped into his seat.

~~~~~~~~

Sam Winchester scratched the back of his neck nervously, fidgeting in his seat before the desk of the guidance counselor, Becky Rosen. His eyes flicked up at the clock on the wall behind her involuntarily. _Eight-oh-seven_. On the desk, there were coffee mugs depicting cats and script-y quotes spread across the surface, mostly half-empty. He went back to his silent observation of the counselor, whose fingers frenetically typed away on her laptop. She held one up to let him know she’d just be another moment, yet it had been at least five minutes and she had yet to even make eye contact. Finally, she shut the laptop and grinned widely to herself before lifting her gaze to the student in her office. Sam smiled back weakly, slightly unsettled by the woman’s too-wide eyes and the way she drank in his appearance. 

“Here you go, Mister . . .” she trailed off as she pulled several sheets of paper from a file and handed him a schedule and looked over his transcript. “Winchester. _Another_ Winchester? Must be my lucky day.” She chuckled to herself as Sam’s brow wrinkled. “Sam, Sam, Sam. Eight schools in ten years! Even a fancy boarding school, my my. Army brat?”

“Uh, not quite—” 

She cut him off with two fingers to his lips and his brows shot up in surprise.

“That’s enough. I’m sure you won’t find Thompson any different from your other schools. Same little _asswipe shit-for-brains_ everywhere.”

“Did you just—?” Sam swiveled his head. “Am I in the right office—?” he stuttered.

She flipped her laptop open again, unperturbed. “Not anymore you’re not. I’ve got deviants to see and a novel to finish! Now get to class, you’re already late.”

Sam gaped.

“Scoot!”

Sam pushed back his chair and stood up quickly, stumbling out of the office as quickly as he could. In his rush, he bumped into another student entering the office. Even though it was his first day, he recognized the boy, a few inches taller than him and wearing an oversized leather jacket and a stormy expression. 

Oh, it was Dean.

Sam gulped and looked up towards his older brother, shooting him an uneasy smile. Dean’s face hardened before turning away without a word. Sam heaved a sigh as he headed out into the hallway. 

That went well.

~~~~~~~~

“Dean Winchester!” The guidance counselor looked at her visitor up and down a few times before her face settled into a disapproving frown. “I see we’re making our visits a weekly ritual.” 

Dean lowered himself in the chair with practiced ease. “Only so we can have these moments together, Beck.” He smiled charmingly. “Should I get the lights?” 

“Oh very smooth, grease monkey. And it’s _Miss Rosen_ to you.” She shuffled through her papers a little shakily before landing on the one she was looking for. “It says here you _exposed_ yourself in the cafeteria?”

He waved his hand dismissively. “That’s bull. I was only joking with the lunch lady.” He grinned lazily. “It was a bratwurst.”

“Bratwurst?” She looked him over, again. “Aren’t we the optimist? Next time keep it in your pants, okay?” Her eyes shone with a glint that made Dean internally roll his eyes and groan. She dismissed him with a curt gesture. “Scoot!”

On his way out, he heard Ms. Rosen mumbling ‘bratwurst’ several times followed by the unmistakable sound of typing. He chuckled to himself as he walked towards his English class, having no doubts that this would end up in her ‘novel.’ 

He purposefully did not think about _literally_ running into Sam as he made his way down the hall. 

~~~~~~~~

In Mr. Henricksen’s class, Cas resigned himself to another forty-five minutes of typical high school ignorance. 

“So what did everyone think of _The Sun Also Rises_?” Mr. Henrickson asked the class, boredom bleeding into his tone. His eyes purposefully skipped over Cas’s face.

“I loved it,” one girl exclaimed. 

Cas figured that either she hadn’t gotten the memo that academic enthusiasm was anathema in public high school, or she was harboring a crush on their admittedly striking teacher. 

“He was _soo_ romantic.”

Ah, the latter. Cas rolled his eyes, fingers pressed to his temple. He tried some self-restraint for his own peace of mind, but his traitorous mouth just couldn’t permit him the luxury. 

“ _Romantic_? Hemingway?!” he scoffed, incredulous. Enthusiasm may have been anathema, but disgust was still celebrated in the teenage realm. “He was an abusive alcoholic and misogynist who squandered half his life hanging around Picasso trying to nail his leftovers.”

Although they were inured to his outbursts, everyone, including Mr. Henricksen, either sighed or groaned. 

Tyson Brady, sitting in the back row, with his standard issue douchebag uniform consisting of slicked-back hair and cocky smirk, decided it was time to chime in. “As opposed to a bitter, self-righteous fag who has no friends?” Some of Brady’s cronies snickered and high-fived him. 

“Pipe down, Brady,” Mr. Henrickson snapped, unamused. 

Cas twisted in his seat to face Brady. “I guess in this society being a heterosexual asshole makes you more worthy of our time.” Turning back towards Henricksen, he added, “What about Rimbaud, or Virginia Woolf? I’m sick of having toxic het _‘romance’_ shoved down my throat.”

“Yeah, we all know what you _really_ want shoved down your throa—"

“That is _enough_ , Brady!” Henricksen slammed his fist down on his desk, to which the White Rasta wannabes in the classroom cheered.

Ever the master of timing, Dean Winchester appeared in the classroom doorway. “What’d I miss?” 

“Only the oppressive heteronormative values that dictate our education and the losers that perpetuate them,” Cas rattled off, shooting Brady another dirty look.

Dean nodded decisively and replied, “Good,” before immediately turning on his heel and leaving. Henricksen called after him, but it was already a lost cause as the door clicked shut. 

Brady spoke again. “Mr. Henricksen, is there any way we could get Castiel to take his meds _before_ he comes to class?” Several students snickered again. 

Henricksen rubbed a hand down his face, his other one gripping the desk edge as if he wanted to take a chunk out of it. “Brady, one day you’re going to get bitch slapped _so hard_ and I’m not going to do a thing to stop it. And Novak—” he finally looked to Cas “—I want to thank you for your point of view.” Cas tensed at the validation until Henricksen continued in a mock-sincere tone. “I know how difficult it must be for you to overcome all those years of upper-middle-class suburban oppression. It must really be tough.”

Cas deflated, shrinking back into the hard seat.

Henricksen kept going, voice rising while his tolerance for bullshit teetered dangerously low this early in the period. “But the next time you storm around the PTA crusading for safe spaces, better lunch meat, or whatever it is you white kids complain about, ask them why they can’t buy a damn book written by a black man!”

The White Rasta kids chimed in again. “That’s right mon!”

Henrickson seethed, flaring his nostrils dangerously. “Don’t even get me _started_ on you two!” They mumbled their apologies. 

Cas snorted.

Henricksen pointed at him, eyes flashing. “You know what, go to the office. You’re pissing me off.”

“Excuse me?”

“ _Get out_!”

Cas stood, gathering his things and making sure to slam into Brady’s shoulder on his way out. Not for the first time, Cas cursed the way the high school’s doors gently clicked shut. Still an adolescent, he wasn’t above slamming doors. 

He trudged down the empty hallway to Ms. Rosen’s office. Henricksen hadn’t specified _when_ he should report to Becky so Cas took some liberties with the mandate, making his way to her office by way of the corner drugstore. Once he finally dragged himself to her office the counselor was busy typing, of course, but lifted a hand to usher Cas inside. Cas seated himself and his belongings. Without even looking up, she addressed him personally. 

“Castiel Novak. Let me guess, terrorizing Victor’s class? Again?” She finally paused her typing and looked him in the face. Her gaze slid to the plastic drugstore bag Cas had brazenly set down at the desk’s edge, but she held her tongue.

“Expressing my opinion is hardly a terrorist action.”

“Oh, like the way you ‘expressed your opinion’ to Raphael? By the way, his testicle retrieval operation went quite well, in case you're interested.”

Cas sniffed. “I still maintain that he kicked himself in the balls.”

Ms. Rosen rested her chin on her hands, considering him thoughtfully. “Is it really worth it? All this . . . pent-up angst and rage? I thought they said grunge was dead.”

Cas did not even dignify that with an eye roll.

“The point is, Cas, the staff and students here perceive you as somewhat . . .”

“Tempestuous?”

"‘Uptight Jackass’ is the term used most often. You might want to work on that.” At his expression, she made a noise of exasperation. “That’s about enough gloom for me today. Why don’t you take yourself and that dark storm cloud above your head out of my office? You’re dampening my inspiration.”

Cas shook his head, his mouth twisted into a bitter smile. “As always, thank you for your _excellent_ guidance.” He gestured with his chin to her laptop. “ I’ll let you get back to Reginald’s ‘quivering member.’” Her mouth dropped open and he turned around to exit the office. He could hear her muffled voice turning the words over and over. How the woman had ever been hired to oversee children was a constant and disturbing source of mystery to Cas. One of these days he and Gilda would finally break into the personnel files to shed light on some of the school’s more unusual hiring practices. 

~~~~~~~~

At the peal of the bell ending first period, students rushed past Sam as he packed up his supplies, eventually standing up from his desk to join their exodus. Just outside the classroom, a slender arm grabbed at his shirt, pulling him off to the side next to a row of lockers. The girl attached to it introduced herself to him. 

“Charlie Bradbury,” she smiled.

“Uh . . . it’s Sam, actually.”

The girl looked at him quizzically, opening her mouth to correct him and Sam shook his head. “It’s a joke. I know you weren’t addressing me.”

She nodded in understanding, then inclined her head to explain, “The office sent me. I’m supposed to show you around.”

“Oh, thank God,” Sam noted she was dressed in a preppy outfit that reminded him of his time at boarding school, but she otherwise seemed normal enough. “You know, usually they send one of those A/V geeks.”

Her smile faltered and she chuckled nervously. “Yeah, ha, wouldn’t want to be stuck seen with one of the _geeks_ on day one.”

A bespectacled boy wheeling a cart with audio and video equipment approached. “Hey Charlie! Where do you want these?” She didn’t swivel her head a millimeter, pretending not to hear him while tugging Sam in the opposite direction. 

“So Sam,” she started, walking ahead. “Let me give you a breakdown.” She pointed over to a group of well-dressed and good-looking people. “Over there you’ve got some of your typical conventionally-attractive people. Unless they deign to speak to you first, don’t bother.”

“That your rule or theirs?” he asked skeptically.

“Observe.” She turned towards the group with a beaming smile. “Hey there!”

“Eat me, geek!” one of the jocks called back.

“See?” 

Sam flared his nostrils, astonished, and was about to confront the jock before Charlie shook her head, shooting him a quelling look. They continued their walk, the jocks and tall attractive girls returning to their bubble like there had never been an interruption. 

Sam took it all in as they emerged from the school into the courtyard and he inhaled a deep breath. The sun was concealed again and rain drizzled softly, the air fresh. Despite himself, he had missed Seattle, even if it had the dreariest weather on the planet. He refocused on what Charlie was saying as she continued her tour like a guide at the zoo. 

“To the left, we have the coffee crowd.” She bumped the side of one of them experimentally, causing a spill. 

“That was Costa Rican, asshole!” he exploded, eyes bugging out, as she continued.

“Very edgy, don’t make sudden moves around anyone that heavily caffeinated.”

Next up, they passed a table full of white boys with dreadlocks and rasta hats. She sighed. “And these delusionals are the White Rasta. B _ig_ Marley fans, think they’re black, act semi-political but mostly they—”

“Smoke a lot of weed?” he cut in.

“Exactly.”

They made their way along, reaching a group of kids hunched over their books, all dressed similarly to Charlie. Her smile faded, but he could tell she was attempting to stay upbeat. 

“And these are your future MBAs. We’re all ivy-league accepted. Yuppie greed is back, you know.” She spoke to the group. “Hey guys, how’re you doin’?” No one answered her, and Sam frowned, his brow creased with concern.

She sighed. “Yesterday I was their God.”

“What happened?” 

“Dick Roman told everybody that I . . .” she bit her lip, considering, “um, care more about watching _Xena_ than studying for my SATs.”

Sam quirked an eyebrow. “So they just kicked you out?”

“Hostile take-over.” She shrugged. “But don’t worry, I have a plan.” She cleared her throat. “Anyways, over here—”

Sam stopped in his tracks when he saw her; the rest of the world ceased to exist. His first thought was that she was the most beautiful person he’d ever seen. Long blonde hair and blue eyes that sparkled like the sea itself. She walked gracefully in a floral dress; something out of a fairytale.

Sam blinked and gulped. “Oh, wow. What, uh . . . what group is she in?”

Charlie barked out a laugh.“The ‘don’t-even-think-about-it’ group. Practically Thompson royalty. That’s Jessica Moore, also a sophomore.”

“I burn! I pine! I perish!” he exclaimed, only half joking.

Charlie scoffed. “Of course you do, Shakespeare. _Everyone_ here is half in love with her.” Under her breath, she added, “Hell, if she could form an articulate sentence I would probably go gay for that.” 

Jess walked by with another girl, in the midst of what Sam could tell was likely a profound discussion. Sam tugged at Charlie to follow behind and overhear their conversation. 

Her voice lived up to her appearance, a waterfall of crisp consonants and lilting tones. “See, there’s a difference between ‘like’ and ‘love.’ Because I _like_ Joseph Gordon-Levitt, but I _love_ Leonardo DiCaprio,” Jess said. 

“But _I_ love _Joseph Gordon-Levitt_ ,” her friend responded, sounding confused. 

“That’s because you’ve only seen _The Man in the Iron Mask_ ,” Jess said knowingly. 

Her friend nodded in realization.

Gagging, Charlie tugged on Sam’s sleeve insistently. “Listen, forget her. She’s completely vapid. Besides, you two would never work. It’s a widely known fact that the Sheriff’s kids aren’t allowed to date.” 

“Huh? Is he super uptight or something?”

“No, _she’s_ super uptight because she’s a city _cop._ And she has to raise someone that looks like Jess. She doesn’t let either her or Cas date anyone.”

“She has a sister?” Sam could hardly conceive of one let alone _two_ such magical beings.

Charlie snorted. “Cas is her foster brother. Total piece of work; you’ve officially been warned. If you think she’s sweet as pie, he’s . . .” she wrinkled her nose. “Rancid as stale wine. _‘Like a boil, a plague sore,’”_ she quoted, then frowned. “Or something.”

Sam had stopped, still staring after Jess, and Charlie shook her head in dismay. “Chick must be a siren, I swear. Every guy here, without fail . . .” When Sam finally acknowledged Charlie with a flick of his eyes she exhaled sadly and patted his arm consolingly. “I would move on if I were you. It’s not like there’s much going on upstairs there, anyway. If you know what I mean.”

Sam looked back to Charlie at that, taken aback. “That’s not very—she’s not _vapid_. How well do you even know her?” He waved his arm. “I mean, just look at the way she laughs. And those eyes. You can tell she’s totally pure. Good.”

Charlie tilted her head back and groaned. “Look, Sam, I thought you were a bright guy. All I see there is a stuck-up princess wearing a strategically planned sundress _on a totally overcast day._ You know why a girl does that? To show guys like you that they can never touch her and guys like…” she swiveled her head back and forth, finally landing on the group of jocks and preppy kids that had migrated outside. She pointed at one of the taller guys who was wearing a varsity jacket and laughing with his friends. “Guys like _Tyson Brady,”_ she spat out his name, “realize they want to.”

Sam shook his head, stubborn. “No offense Charlie, but I think you’re wrong about her. I just have this _feeling.”_ He rolled his eyes at her arched eyebrow. “Not like _that_. Well. Not just.” 

Charlie threw up her hands. “I tried! You wanna waste your time? That’s no skin off my nose. I’ll even give you a head start. I think I heard she’s looking for a French tutor or something.”

Sam clasped Charlie’s shoulders. “Are you serious? That’s . . . that’s perfect!”

“What, you speak French?” She looked skeptical.

Sam pulled her in for a hug and she yelped in surprise. “Well, no. But I will.” 

~~~~~~~~

The rain had swelled to a steady drizzle accompanied by fog that smudged the edges between the sky and evergreen treetops. Jess had reluctantly slipped a sweater over her cheerful dress but the single layer wasn’t quite sufficient against the rain. Beside her, Rhonda clutched an umbrella over both their heads, sleeve pulled taut down over her knuckles. 

Billie had volleyball practice and wouldn’t be leaving school for another hour, which left Jess and Rhonda with the bus for a ride home. Jess steadfastly ignored her brother with his friend Gilda getting into his car. As debasing as it was to be riding the schoolbus, it was still preferable. She felt something twist in her gut watching the two of them laugh, hands shoved into the pockets of their hoodies.

An unmistakable bright red sports car slowed to a stop beside them and the windows rolled down to reveal a smiling Tyson Brady. “Hey. Jessica Moore, right?” His eyes looked her up and down, then over to her companion. “And . . . Rhonda?” He gestured with his thumb at the sky. “It’s a little wet for bare legs, don’t you think? You sweet young things need a lift?”

The girls exchanged a quick conversation through their eyes then nodded emphatically. Brady grinned and the doors clicked, unlocked. Eagerly, Jess and Rhonda clambered in, Jess up front in the passenger seat. Brady glanced back at Rhonda sliding into the middle seat with her bag. Startled, he cried, “Whoa! Watch the leather there, Jesus.” Rhonda apologized, then shot a dirty look at the back of Jess’s headrest. Before pulling away Brady made sure to wave at his friends’ retreating forms as they dispersed to their own cars. They smirked back, thumbs up and hollering something back, too soft to pierce the rain and car windows.

Pulling up behind them, Cas stared down the back of Brady’s head through his windshield. He ground his teeth while watching the exchange between Brady and his sister and her friend, and next to him Gilda choked out in disbelief. 

“That’s a charming new development,” she spat. 

Cas continued to glower. “It’s disgusting.”

Cas could tell from the way Gilda chewed her non-existent nails that she wanted to say something but was holding back. She knew better than to suggest Cas intervene. On the one hand, nobody on Earth got under his skin like his sister and he’d long given up on trying to influence her actions. On the other hand, Brady was . . . Brady. Pain, anger and irritation bubbled dangerously near the surface whenever he dwelled on that particular malefactor. The two of them together was nothing short of catastrophic, at least for his blood pressure.

Brady was finally pulling away, revving his engine obnoxiously and Cas accelerated behind him, itching to put distance between himself, the infernal sportscar, and the school. Gilda flung her arms out, shrieking, and Cas slammed on his brakes as a flash of yellow darted mere feet from the Continental’s front bumper. The lunatic riding the motorbike then _stopped,_ probably stalling out. The rider scrambled at the wet pavement, resorting to walking the thing away from Cas’s car. Cas, already fuming, rolled his window down and swung his head out to yell, “Remove head from sphincter, _then_ ride!”

The rider swung one terrified look to Cas before moving out of the way and he drove off. It spoke volumes to his self-control that he was able to steer through the rest of the school parking lot at a semi-reasonable speed before finally escaping onto the wet streets of Seattle. 

~~~~~~~~

“Charlie! Oh my god, are you okay?”

Charlie tugged off her helmet with slippery fingers, straddling the yellow bike. She replied, “Oh yeah. Fine. I’m, I’m good,” yet her shaky limbs suggested otherwise. 

“That guy was a total jerk.”

“ _That guy_?” Charlie raised her brows, then barked out a hysterical laugh. “ _That guy_ is none other than Castiel Novak. Your dream girl’s older brother. No one here likes him, even the teachers. I give it a week, _tops_ , before you do something to make Mister Anger Management bite your head off too.”

Sam winced at the imagery, hand raising to rub at the back of his neck subconsciously. 

~~~~~~~~

Charlie still shook from her incident with Castiel’s car after Sam had caught the bus home. It was already shaping up to be quite the week. She exhaled unevenly as she refastened her helmet and hopped back on her bike, grip firm. Triple checking each direction, she pulled out of the parking lot and slowly cruised through the busy streets, struggling to focus while her mind spun in turmoil.

It had been stupid to stall out like that, as if she’d learned to ride yesterday. One second she was crossing over the lane to say goodbye to Sam and the next she was frozen, gaze fixated on delicate brown eyes through a smudgy window that widened in unmistakable terror. The screeching of brakes on wet pavement, Castiel apoplectic and screaming at her like a wild animal. But Gilda was so—no, _no_. She couldn’t think about that too much right now. That was a whole can of worms she couldn’t afford to open right now. 

She had more pressing problems with her social life. She had never seen eye to eye with Dick Roman and with a few well-placed rumors he had effectively turned half of her friends against her. The other half were still stuck up, spoiled jerks anyways. It was all clique-y bullshit. 

So what if she spent her Monday nights watching _Buffy_ instead of getting ahead in microeconomics? Or spent more time playing _Dungeons and Dragons_ than sharpening her calculus skills? She could still be a badass future MBA all while loving those things. 

She remembered Sam then. Never in her life had she seen someone’s eyes convert into hearts like that—the guy gave new meaning to ‘puppy love.’ From the gossip she’d overheard in the staff lounge, the guy had been through some shit. An innocent crush was probably a nice change for him. Heaven knows the boy could use a little help and it looked like she could really use a friend. 

~~~~~~~~

Cas was seated crisscross on the floor, leaning against the couch reading _A Single Man_ when the front door opened. Today was his day off from volunteering at the senior center and he was glad to have extra time to spend reading something that wasn’t approved by the school board.

Sheriff Jody Mills entered, balancing a stack of mail and scraping her boots on the doormat. “I’m home!” She walked into the living room, spotting Cas. “Hell-o Castiel, make anyone cry today?” she asked jokingly. 

Cas replied without looking up from his book. “Not to my knowledge, but I’ve still got some time. It’s only…” He spared a glance to his wrist, which was noticeably absent any watch. “. . . four-thirty?” 

Jody snorted, smile immediately brightening as Jess entered the room followed by Leo, their sheltie. “Hi Jody!” Jess said sweetly as she pulled her into a hug, Leo barking about their heels at the contact. 

“Hey sweetheart. Leo, _off_!” 

Cas spoke, careful to preserve a nonchalant tone. “She returns home at last.” Starting a fight with Jess wasn’t strictly a wise idea. It disturbed him how bothered he was by her new . . . _whatever_ with Brady. The mere reminder had his fingers twitching. He set his book down when Leo approached him, sniffing at his outstretched hand. The dog settled at his side, watching the women with apprehension. The dog had an exceptional talent for noticing when a family screaming match was brewing. Cas threaded his fingers into the white fur at his neck, grounding himself. 

Jess merely curled her lip and rolled her eyes at his words, ignoring him. 

Jody wisely overlooked this exchange as she sifted through the mail, tossing heaps of junk mail onto the dining room table with a noise of disapproval. Into this pile slipped a particularly fat envelope, which she withdrew, forehead wrinkling as she flipped it over to read the label. She glanced down at Cas, then said pointedly, “What’s this? A letter from Tufts?”

Cas twisted and craned his neck to face her. “What? Give it to me.” She complied without a word and Cas read the label, leaping to his feet. He tore open the envelope and scanned the first lines of the letter. He clapped a hand to his mouth, re-reading the line that incredibly began with _‘It is our pleasure to formally inform you of your conditional acceptance as a student…’_ again and again, unable to continue onto the rest of the paragraph. He began pacing about the room, his agitation prompting Leo to jump to his feet and yap at Cas. 

“I got in.” The words didn’t get out past the lump that was quickly forming in his throat. He swallowed and repeated the line, then looking up at Jody and Jess who stood too quiet, watching his outburst. “I got in!” 

Jody’s smile was tight. “Honey, that’s great, of course you got in. But isn’t Tuftsa private school?” She spoke the term as if it were some infectious disease. _“_ A _very expensive_ private school _,_ and on the other side of the country?”

Cas blinked. “Thus the basis of its appeal.”

Conflict was written all over Jody’s face. “But I thought we decided you would stay here and use that scholarship, go to UW like me.”

“No, you decided.”

Jody crossed her arms, looking thoughtful.

“Does this mean Cas is leaving the timezone?” Jess asked, voice brimming with hope.

Cas shot Jess a glare, then turned toward Jody, smiling sweetly _a la_ Jess. “Ask Jess who drove her home.”

“Cas!”

“Don’t change the . . . hang on, drove?” Jody zeroed in on Jess like a hound, the cop in her showing. “Who drove you home?”

Jess’s face went white, her entire body looked ready to run. Cas held back a smug smile, relieved that Jody was so easy to redirect even after all these years. “Jody, please don’t get upset, but there’s this guy—”

“—who’s a raging asshole,” Cas added helpfully.

Jess continued, voice tight, “—and I think he might ask me—”

Jody waved her arms in protest. “Whoa! I think I know what he’s going to ask you. And I think I know the answer: no. It’s always no. Jesus Jess, what are the house rules?” She counted off her fingers. “Number one, no dating ‘til you graduate. Number two, _no dating ‘til you graduate_. That’s it. If you can recite all the lines in _Titanic_ you can remember one rule.”

Cas cracked up as Jess reddened.

“Jody, that’s so _unfair—_ ” Jess argued.

Jody cut her off. “ _Unfair_? You wanna know what’s unfair, Jessica Moore?” She gestured to Cas as well. “This morning I had the pleasure of overseeing the boys as they hauled a nice young lady like yourself out of Green Lake, where her boyfriend _dumped her_ after finding out she was pregnant.”

“I fail to see how any of that applies to me.” Wincing at himself, Cas cleared his throat and added, “Uh, condolences though. Respectfully.”

Seething, Jess opened her mouth to protest but Jody held out a finger. “Even assuming that you don’t land yourself some homicidal date, which I am certainly _not,_ dating leads to sex, and sex leads to pregnancy.” Looking at Cas, she added pointedly “Or disease. And before you try and say anything about _protection_ I’d like you to take out those pamphlets again about condom success rates and human error. And I’m sure you’ve both heard of _stealthing_ by now.”

At this, both Cas and Jess actually mirrored each other’s expressions of distaste. 

“Can we come back to reality here and focus on me for a second please?” Jess complained, “I’m the only person over seventeen who’s never gone on a single—”

“Hold up, the only person? Cas doesn’t date,” Jody pointed out. 

“And I don’t intend to,” Cas added sagely.

Jody prompted, “And remind us why that might be?”

Cas clutched a hand to his chest and cried out overdramatically, “Have you _seen_ the unwashed miscreants that go to our school?”

“I HAVE TO LIVE UNDER THE SAME ROOF AS ONE OF THEM!” Jess shrieked.

In the ensuing silence, Cas watched contritely as Leo bid a hasty retreat to the kitchen, and Jody laid a gentle hand on Jess’ arm, guiding her onto the couch. Her voice was even. “You know what? New rule then.” Jess crossed her arms, skeptical. “You’re allowed to date—” Jess held her breath while Jody exhaled “—when he does.”

Jess’ expression contorted into one of fury and she leapt back to her feet. “You’ve got to be kidding me! What if he _never_ dates?”

Jody looked exceptionally pleased with this new rule. “I guess that means . . . you never date? Ooh, I like that. I’ll sleep well at night. The deep slumber of a parent whose kids aren’t out being impregnated or infected with HIV.” She stood, collecting her mail and added, “I do this because I love you both too much, okay? All the things I’ve seen happen to nice young people, I would be negligent to let that happen to you.” Jody’s pager went off, indicating a call. 

Jess turned to Cas, chest heaving and mouth pressed into a furious thin line. “Can’t you find some other _gay loser_ to take you out so I can have just one date before I shrivel up and die?”

Cas shrugged. “Sorry Princess. Looks like you’ll just have to miss out on the witty repartee of Tyson ‘eat me’ Brady.”

“You suck!” She stormed away, face hot and unable to look at her so-called brother a moment longer. 

“ _You suck.”_ Cas mocked her in a sing-song tone as she went, unable to resist. He headed into the kitchen, opening the fridge to grab a drink and cajole the dog out from under the table. He led him back towards the couch and picked up _A Single Man_ again, the two of them settling into the plush cushions. He was surprised to find his hands were trembling and he closed them into tight fists before reclining his head with a long exhale. 

~~~~~~~~

After skipping out on the inane discussion in English, Dean had gotten ahead on the next few weeks worth of classwork. It wasn’t like it was hard, and it had given him the time to pick up a few extra hours at the car wash and get dinner together. Dean finished up cooking and made his way to the dinner table with the steaming dish of lasagne, where Henry and Sam were waiting for him. 

“Smells great, Dean.” Sam said, apprehensively. 

Dean grunted. He was still too angry at the kid, and he didn’t have the energy for another fight. 

Henry tried to break the silent tension at the table. “So Sam, how’d the first day back go?” 

Sam cleared his throat, purposefully only looking towards Henry as he responded. “Pretty good, considering it’s the middle of the semester. Think I made a friend, which is a good start.” 

Henry nodded along and Sam continued to chatter about various encounters he’d had that day with students and teachers alike, neatly omitting his brief run-in with Dean in Rosen’s office. 

Dean clenched his jaw, but didn’t comment and instead focused on his plate. Dean finished quickly and bolted out of his chair, muttering a lie about having work to finish. 

~~~~~~~~

Sam flipped through his newly-acquired French textbook and reviewed all the notes he’d taken over the past few hours in last minute preparation for his tutoring session with Jess. He’d studied Latin in boarding school, had actually been pretty damn good at it, and French came from Latin, right? There was no reason for his heart to be pounding.

He noticed the moment she entered the tutoring center—he had whipped his head up reflexively at every person for the past ten minutes—and tried unsuccessfully not to stare rudely as she gracefully slid into the chair next to him. 

“Hi.” She rewarded him with a big smile, which faltered slightly when she glanced to the books strewn on the table. “Can we make this quick?” At Sam’s expression, she explained, “Kali and Gabriel are having an _incredibly_ horrendous public breakup on the quad. Again.” She looked at him through long eyelashes, pleading. 

Sam gulped. “Uh, sure okay.” He flipped back quickly through the textbook, fingers catching awkwardly on the pages in his haste. “I thought we’d start with pronunciation, if that’s alright with you.” She scrunched up her face, which usually didn’t present the most flattering expression on human beings but Sam was smitten nonetheless; irrationally it made her look even cuter. 

“Not the hacking and gagging and spitting part, please.” 

He smiled, a thought occurring to him. “Well, there is an alternative.” 

“There is?” She tilted her head, quizzical. 

He inhaled, twisting his fingers together. “French food. We could eat some together? Saturday night?” He watched for her reaction. 

Her brows raised in realization. “You’re asking me out?! That’s so . . . cute. What’s your name again?” 

“Sam,” he pursed his mouth. “Listen, I know your mom doesn’t let you date. But I thought that if it was for French class it would–”

At the mention of her mother Jess clasped Sam’s wrist, interrupting. “Oh! Wait a minute, Sal–”

“It’s Sam,” he repeated softly, momentarily transfixed on her slender hand on his.

“My mom just came up with a new rule: I can date when my brother does.”

Sam brightened at this lucky turn of events. Having braced himself for a rejection, his chest loosened at her words. He faced her head on finally. “Great! Well let me ask you, do you like sailing? ‘Cause I read about this place that rents out boats–” 

Jess retreated a fraction of an inch, face shuttering. “No Sean, I don’t think you understand. I can’t date until _my brother does._ In case you haven’t heard, he’s a particularly hideous breed of loser. And gay.” Sam deflated a bit, now recalling Cas from the parking lot. “Yeah, yeah. I noticed he’s a little . . . anti-social. Why is that?” “Unsolved mystery. He actually used to be really popular, and then it was like, he got sick of it. Or something. There’re bets as to why, but I’m pretty sure he’s just incapable of human interaction.” 

From her frank expression, Sam would have guessed she was talking about last night’s Mariners game rather than a family member. His brow knitted together and with his free hand he started tapping the table with his pencil. Thinking aloud, he said, “Well yeah, but I’m sure, you know, that there’s lots of guys who wouldn’t mind going out with a…difficult guy. Don’t all the studies these days agree that men are all about the thrill of the chase? I mean, you know, people jump out of airplanes, ski off cliffs. It would be like extreme dating.” Jess quirked a brow, glancing around the library. “You think _you_ , the new kid, could find someone _that_ extreme?”

Sam ignored her obvious skepticism, his mind automatically conjuring the image of his brother. He quashed the thought just as quickly. The two of them were barely speaking; he doubted Dean was anywhere near willing to do Sam any favors.

Persistent, Sam shrugged. “Yeah sure, why not?”

She reached out and placed her hand on his arm and her blue eyes were beseeching. “You would do that? For me?”

Was there anything he _wouldn’t_ do for this girl? “Hell yeah!” He winced at his eagerness, rubbing his hand down his face. “I mean, you know, I could look into it. Thrill of the chase, and all that.”

She mouthed the words to herself, then smiled knowingly. “I’m counting on that scientific consensus.” She squeezed his hand again and said, “You’re the best!” before rising out of her seat and gathering her things to take her leave, finally withdrawing her hand from him with a caress. “See you later, Sam.”

Unable to help himself, or to still his rapid heart rate, Sam stared after her as she sauntered away. He packed up his own things haphazardly, nearly forgetting the French book altogether, and rushed out of the tutoring center. He had to find Charlie.

~~~~~~~~

“Sorry, you need me to help you _what?”_

Sam pressed, “One guy, that’s all we need. There’s no way he’s the _only_ homosexual in the school.” He had seen and heard too many things during his time at boarding school to believe that. 

Again, his thoughts went to his brother. Dean had once explained to him that he saw no point in limiting himself to girls and ignoring half of the population. _Sammy, it would be like swearing off cake, just because you love pie. And pie’s awesome, don’t get me wrong; it comes in lots of flavors, a la mode, all kinds of crusts. Nine times out of ten, I’m down for pie. But sometimes you’re just in the mood for cake, you know? Craving that rich frosting…_ Sam had gagged at that, while Dean just tossed his head back and laughed and laughed. 

Sam felt a familiar pang at the memory, a bittersweetness at recalling happier times with his brother when their relationship now was so fractured. “It’s just, after the tour and everything, you seem to have a really good handle on this school. You seemed like the best person to ask.”

“This is such a long shot. You wanna do this for some _girl?_ ”

Sam dropped his head. 

“Fine, fine. I won’t say I get it, ‘cause I don’t.” Charlie shifted the mountain of books in her arms and bit her lip. “Maybe I can call in a few favors. Meet me behind the theatre, after fifth period before AP Bio.”

At Sam’s expression, she sighed, though not unkindly. “If you head down Hall C by your English class, that runs into the hall with the auditorium and the gym. Go left toward the auditorium and the doors lead out back.”

Sam saluted her and Charlie reluctantly smiled before they parted ways at the sound of the bell.

~~~~~~~~

As agreed, Sam met up with Charlie outside the school and followed her as she motioned him down a set of musky concrete steps, a Thompson yearbook tucked under her arm. 

Before descending, she whispered to him, “Keep a straight face. And an open mind.” She pulled him along and they descended. She explained loudly, “Now I’ve gathered a group of guys. Couldn’t be more perfect. Thompson’s finest.”

They rounded the corner into a corridor where a group of boys were all standing like a prison lineup, their faces sullen. Sam did a double take, looking to Charlie for further explanation. She stood there mutely, smile plastered on. ‘Thompson’s Mediocre-est’ would have been a stretch; gathered before Sam were some of the most depressing-looking guys he had ever seen. Two of them looked to be about twelve years old, tops. One guy had a face so hideously pockmarked Sam felt a jolt run up his spine and barely kept himself from recoiling. Maybe he had a funny personality? The one in the middle had his hand shoved into a massive bag of Cheetos, which he brought up to his face. Both his hand and mouth were dusted fluorescent orange. Meanwhile a guy at the end looked so pale and skinny that Sam was contemplating calling the authorities before he collapsed from starvation. 

Sam would need a much stronger imagination to picture any of them wooing Castiel Novak. On a brighter note, Sam wondered if these guys were so desperately pathetic that Castiel would agree to date one out of sheer pity. Anything was worth a shot if it meant a date with Jess. What did he have to lose? 

“Hey. How’re you guys doing?” One of the boys crossed his arms while the rest stared at him coldly. Sam gulped. “I guess we’ll just grab one of you at a time then?”

Charlie motioned to the first one and they led him around the corner for a mini-interview. He had bug-eyes and super baggy pants that obscured his shoes as he shuffled after them. 

Sam cleared his throat, then asked, “Would you, uh, be interested in dating Castiel Novak?” Sam and Charlie both flinched as the guy began laughing hysterically, head pitched back and sides convulsing. 

The next boy simply opened his mouth in silent horror before taking off sprinting back up the stairs. 

More laughter.

Cheeto Guy crinkled up his bag and flung it at Charlie’s face, which she narrowly avoided. “Hey!” He sauntered away, chuckling, and said, “Are you fucking high? I’ve never been that whacked.”

Before Sam opened his mouth, the next one asked, “How much?” At their puzzled expressions, he pressed, “Aren’t you gonna flash me?”

“ _Who_?”

Charlie opened the yearbook, then pointed to a picture. The boy screamed. Sam and Charlie clapped their hands to their ears at the bloodcurdling noise until Charlie thumped him with the yearbook and he, too, set off running. 

The one with the severe acne problems replied to the question, “Maybe if we were the last two people on Earth and there were no sheep.” He looked between Sam and Charlie, brows raising. “Wait, are there sheep?”

Sam turned to Charlie, grimacing, and drew a line with his finger across his throat. In answer to his prayers, the bell rang and the two of them rushed off to Bio.

~~~~~~~~

They narrowly slipped into their seats in time, out of breath. 

“ _Really_ Charlie?!”

She raked a hand over her face. “Did I, or did I not, tell you this was pointless?” She cleared her throat noisily as they began to dissect the frog. “No one from Thompson’ll go out with him. You’d have better luck finding him a date in the condom section at Walgreens.”

Sam turned halfway to see the teacher scrawling on the whiteboard and was startled to see Dean sitting down a table over, staring at him. Eyes fixed on Sam, he picked up the butterfly knife and impaled the frog on the tray in front of him. 

Charlie trailed off, noticed his gaze locked on Dean, and reached a hand to clasp on Sam’s. “Hey! No. Don’t look at that guy, okay? He’s a criminal. I heard he set a state trooper on fire. He did a year in San Quentin.”

Dean? _In jail?_ Wouldn’t he tell Sam something that big? Who the hell did he think he was, acting like he was so much better than Sam then? He swallowed, trying to tamp down on his spiking anger. It swiftly morphed into guilt as he reflected on his brother’s actions, that time at the hospital. Whatever trouble he had or hadn’t gotten into was nothing compared to Sam’s last couple of years. Unprepared to divulge his past to Charlie, he played it cool, reining in his emotions and exhaling deep. Voice tight, he replied, “Well, it’s probably been awhile since he was laid?” Gross. He _so_ didn’t want to think about his brother like that. 

Charlie flipped to the back of her worksheet, reading as she spoke distantly, “I’m serious, he’s whacked. They say he sold his own liver on the black market for a new set of speakers.” 

Sam wrote his name at the top of his sheet, fighting the urge to laugh. That sounded far fetched, even for Dean. His brother was definitely too much of a germophobe to deal with some sketchy black market operation. Sam covertly watched as Dean took out a cigarette and lit it on the bunsen burner flame. Flames danced in his eyes, which crinkled as he chuckled in response to something the guy next to him said.

“No, he’s our guy,” Sam said decisively. “Trust me.”

“As you wish,” Charlie shrugged. 

~~~~~~~~

The next day, Charlie met Sam next to the shop class door. They had agreed earlier that they needed to confront Dean away from Jess and Cas, which eliminated biology as an option. Sam had snooped around and deduced Dean’s class schedule and was pretty sure Dean had shop this period. As confirmation, Charlie peeked in the window and said, “Yep, he’s in there. Come on.”

They slipped inside, squinting against the clouds of sawdust and intermittent screeching from the opposite wall as the teacher demonstrated the table saw to a circle of students. Charlie breathed out in relief when she saw Dean isolated at his own workbench arranging his tools, away from the teacher. She prompted Sam and he cleared his throat as they shuffled towards Dean from behind. 

“Hey! Dean! How’re you do–” Dean swung around then, brandishing a power drill, posture decidedly hostile. His eyes flicked between Sam and Charlie before narrowing. 

Sam gulped, then started again. “I was wond–”

Dean pushed down the button on the drill, drowning out his voice. 

“I was wondering if–”

Dean repeated the action, his expression unchanging. Sam gaped, looking briefly to Charlie with panicky eyes.

“Dean, I jus–”

Dean thrust his hand out then, driving the Forstner bit right through the middle of Sam’s new French textbook, which was clutched in front of his chest like a shield. Dumbstruck, he lifted the ruined book to his face. Charlie blinked in surprise as she saw a flash of amusement in Dean’s face. She tugged Sam’s shoulder back, shaking her head and gesturing at the far wall. The students there had dispersed and the teacher had his arms crossed and was squinting in their direction. 

“Fine. See you later then,” Sam said as he backed away.

They hastily retreated from the shop room and made their way to the cafeteria. Sam said nothing, but was clearly shaken by more than just the usual questionable slop being scooped onto their lunch trays. She finally broke when they sat down. “Well, that was different.”

Sam snorted, stabbing his plastic fork into what vaguely resembled mashed potatoes.

“Soooo,” Charlie drawled, prying open her milk carton. “What’s the deal there? With you and Dean? You’re nervous around him, but not like everyone else around here. Have you already met?” She tipped the carton back.

Sam rubbed his neck. “He’s, uh, he’s my brother.” 

Charlie spluttered and milk flew out everywhere. She scrambled for a napkin and leveled Sam with a half-apologetic, half-accusatory gaze. At no point during this harebrained operation did he think _that_ was valuable information to share? He looked even more uncomfortable, so she didn’t pry. Instead she asked, “How do we get him to date Cas? If he’s your brother can’t he, I don’t know, do you a solid in exchange for helping him sneak out for beer or something?” She picked up his textbook and stared through the hole. “You have any dirt to blackmail him with?”

Sam shook his head. “I don’t know. Obviously he’s not talking to _me_ right now. Maybe he’d listen to someone else.”

She nodded thoughtfully before an idea slowly dawned. “Well, then, what we need is a backer.”

Sam frowned. “A backer?”

“You know, someone with money who’s stupid.” She smirked and pointed her thumb over to where Tyson Brady was sitting. “Watch and learn.”

Charlie approached Brady’s table with as much confidence as she could muster. As she got closer she noticed Brady and his pals were drawing what appeared to be women’s breasts on the plastic lunch trays with markers. She sighed. How classy. Girls honestly wanted to _date_ guys like this?

Charlie sat down at the one open chair, planting her legs apart in a posture she hoped radiated cool and casual. She totally had this. She gulped. “Is that a _peach_ fruit-roll up? Cause you don’t see many–” One of Brady’s buddies locked her wrist in a vice before she could reach for it. “Okay yeah, alright,” she said and raised her other hand in surrender. The crony released her hand and she cradled it to her chest, wincing.

Brady looked a Charlie in disbelief. “Are you lost?” he asked, tone suggesting that she had wandered down the wrong hallway from the mental ward. 

“No, I actually came by to chat.”

Brady gestured between them with his finger, brows knitted. “We don’t _‘chat_.’” 

“Okay, you’re right. It’s cool. I actually thought I’d run a business idea by you. Just to see if you’re interested,” she pushed.

“I’m not,” he snapped, patience waning.

“I’ll give a pitch—no more than thirty seconds! You want Jess, right?” She looked at him expectantly. “And her mom has this new rule that she can date now, as long as her brother starts dating first. So she can’t go out with you because her brother’s an asshole and no one will go out with him, yeah?”

He cut her off. “Does this conversation have a purpose?” “What I think you need to do, is hire someone to go out with Cas. Someone who doesn’t scare so easy.” She tilted her head towards the left where Dean sat a few empty tables over spitting out the pit of a peach onto his tray with his friend Ash.

“That guy?” He protested incredulously. “The one who just got out of prison? Didn’t he eat a _live duck_?”

“Nah, that was that pepperjack monstrosity from Biggerson’s that had–” Sensing Brady’s increasing vexation she stopped herself. “Never mind.”

Brady turned back to look at Dean. “What’s in it for you?”

She considered. “I’m walking down the hallway and say hello to you. You say hello to me.” A little ego-stroking always went a long way with jerks like this guy. 

“Okay, yeah I get it. You’re cool by association. I’ll think about it.” He tried to sound aloof but he was clearly already sold on the idea.

She smiled, pleased, and bobbed her head. Convincing Brady was easier than she thought it’d be.

He eyed her with distaste. “We’re done now.”

“Yep,” she said and walked back to Sam.

“‘ _Watch and learn?_ ’ Why did you get him involved?”

“Relax. We’re just letting him pretend he’s calling the shots. While he’s doing our work for us with your brother you’ll have time with Jess.” She smiled reassuringly. 

Sam nodded. “You’re right. This is probably my best shot.” He wrinkled his nose at his lunch tray and pushed it away.

Charlie washed another bite-full down with the last dregs of her milk. “As thanks, maybe you can do something about getting us something edible for lunch every now and then.”

Sam laughed. “I probably owe you a lot more than that. Especially if this plan actually works.” More serious, he added, “Really, _thank you_ for all this. You’ve been an amazing friend to me.”

Charlie’s cheeks warmed and she looked away. “Yeah, yeah, I know. I’m awesome.”

~~~~~~~~

Lighting another cigarette, Dean settled next to Ash on the bleachers while they ditched their Spanish class. He didn’t feel like listening to everyone’s terribly pronounced ‘ _mi memoria favorita de la familia_ ’ presentations much less giving his own.

Today the women’s track and the men’s soccer teams shared the field. Dean’s appreciative gaze on the various members of both teams was abruptly obstructed by a stuck-up looking guy in a white tank hovering in front of him flanked by a couple of constipated-looking companions. 

“Hey, what’s up?”

Dean didn’t respond, instead scooting over a foot and opting to communicate _‘get lost’_ on the strength of his arched brows alone.

Evidently too inept to read the road signs, Cocky White Tank tried again. “You uh, been to Biggerson’s lately? I thou—”

Dean leaned back on his hands, affronted. He couldn’t imagine Mr. Overcompensating here was actually _hitting_ on him; Dean was lost as to his intentions. Incredulous, he asked, “Do I know you?”

“Tyson Brady?” The guy frowned at Dean’s lack of familiarity with the name, as if he’d just told him he was Ricky Martin. White Tank—Brady, rather—blinked for a beat then collected himself. 

“See that guy?” Brady pointed towards the field, indicating towards a tall blur of tan and dark hair sprinting down the field. Dean squinted. 

“That’s Castiel Novak. I want you to go out with him. On a date.”

“Yeah, sure thing Sparky.” Next to him Ash started cracking up. It was common knowledge that Dean was an equal opportunist in the romance department, so Dean failed to see the humor in the joke. He narrowed his eyes at Brady’s posse, half-expecting to see hidden cameras. 

Brady shifted, crossing his arms. “Look, I can’t take out his sister until Castiel there starts dating. Their mom is nuts, she has this rule where she won’t let them—"

Dean interrupted, “No offense, but I don’t give a rat’s ass about your sob story. It’s not my problem.”

“Sure about that? Would you be _willing_ to make it your problem?” Brady dug out his wallet, holding it in front of Dean pointedly.

Dean barked out a laugh in disbelief. “You’re going to _pay_ me to take out some dude? Do I _look_ like some Rent-A-Date gigolo? Pass.”

“No, Jesus. You’re not having sex with him, just taking him out to a movie or some shit.”

Once again, Dean wanted to tell this guy to take his weird idea of a prank and get lost, but a niggling voice at the back of his head stopped him. This guy was offering him money to take someone on a date. 

“Just a date? Singular? No strings?”

Brady nodded.

Beside Dean, Ash spoke up abruptly. “This isn’t like some straight or closeted kid you’re trying to mess with?” 

If Dean didn’t already know better, he would have wondered the same thing. He wouldn’t put it past this douche to find something like that funny.

Brady practically stamped his foot, irritated by the line of questioning. As if he wasn’t the one who approached Dean asking for a _favor._ “Ask anyone—he’s queer as a three dollar bill. Never shuts up about it, either.”

Dean conceded the point. One date, not a prank. It wasn’t his usual style, especially when it came to guys. But if it were _a lot_ of money . . . he thought of Henry. Hating himself, he avoided looking at Ash and asked, “How much?”

“Twenty bucks.” Right as Brady replied Dean watched as the subject of their bargaining tore down the field and violently body-checked one of his teammates to the ground, face stricken with pain. Dean raised his eyebrow meaningfully at Brady, who exhaled sharply and relented. “Fine. Thirty.”

Dean could earn more than that in a night at a car wash without having to play make-believe and fake-laugh at someone’s lame jokes. Yeah, right. He laughed. “This chick is only worth thirty bucks to you? Let me spell this out for you.” Dean started counting off his fingers one by one. “Dinner and a movie—that’s fifteen bucks for tickets. Oh and gas money—I drive a pre-’73 oil crisis ride,” Dean saw no flicker of recognition and resisted the urge to roll his eyes before continuing, “So that adds up. Popcorn and drinks, fifty-three. And he’ll want, uh, raisinettes, so what you’re really looking at is,” Dean rested his chin in his palm and affected his best math face. “Seventy-five bucks. Just to cover my costs.”

“This isn’t a negotiation. Take it or leave it, trailer park.” 

Dean bristled at the insult and thought about standing up and asking him to repeat it, but he refrained. He wasn’t the meathead here. Instead he plastered on a grin and reached out a hand. “Seventy-five bucks and you’ve got a deal, Fabio.” Dean watched the gears working in his head for a beat before Brady finally handed over the cash and stomped away. 

Dean smiled to himself, pocketing the cash. He could feel Ash’s gaze burning a hole in his arm, but he ignored him. Any day he got to take seventy-five bucks off the hands of a guy like that was a good day. 

There was a sharp whistle and the boys on the field stopped running. Ash must have directed his eye-lasers away at some point, because he pointed a skinny finger out at the field and said in a flat tone, “I think your new boyfriend just broke some poor schmuck’s arm.”

~~~~~~~~

Dean waited on the bleachers until practice was over to head down the steps towards Castiel, snuffing out his cigarette along the way. He rubbed his hands together and plastered on his most charming grin. “Hey there handsome, how you doin’?”

Castiel narrowed his eyes. “Exhausted and sweating like a pig actually. And yourself?”

“Now there’s a way to get a guy’s attention.”

“My mission in life,” he declared, tone sarcastic. “But I’ve obviously struck your fancy, so it clearly worked. The world feels right again.” Castiel hefted his bag up onto his shoulder and began to walk up the concrete stairs. Dean hurried after him. 

“So pick you up Friday then?”

“Right. Friday, uh huh.” Castiel sounded unamused. 

“That’s the night I take you to places you’ve never been before.” Dean was aiming for smooth but the line came out more like a wheeze as he struggled to keep up with Castiel.

“Like where? The 7-Eleven on Broadway? Do you even know my name?”

“I know a lot more than you think.” Dean was glad Castiel couldn’t see his grimace as he stood hunched over, hands on his knees while he caught his breath. Either Castiel underestimated his own renown at Thompson or he seriously questioned Dean’s intelligence. Or maybe Dean was missing a lot more class than he realized. 

Castiel spared no backwards glance before disappearing from sight, leaving Dean standing alone. The stadium lights powered down, shrouding him in partial darkness. Seventy-five dollars was starting to feel like a lot less money.

~~~~~~~~

Dean drove home, contemplating whether he would spend the rest of the evening relaxing or thinking about how to deal with the dick he was supposed to convince to go on a date with him. He climbed up to the apartment and unlocked the door only to find Sam waiting, arms crossed, in the front room. 

Without sparing him a cursory glance, Dean jibed, “Hey Mom, sorry it’s after curfew.”

Sam ignored him and insisted, “Dean we need to talk. You can’t keep walking away from this.”

Silent, Dean kept walking away from ‘this.’ 

“Dean, I want to work on fixing this. I made so many mistakes and I want to make it up to you,” Sam pleaded.

Shoulders tensing at his words, Dean looked to the window, seriously considering clambering out.

“I realize you’d rather sink into the center of the Earth than have this conversation,” Sam surmised. “But if we never speak again life for Henry is gonna suck.”

Dean narrowed his eyes. Sam must be desperate if he was pulling out the Poor Grandpa Henry card.

“Okay, let’s have it your way. We always do in the end, huh?” He faced Sam head-on and blurted, “What about what _I_ wanted back then? When I bought a plane ticket out to that hospital in _fucking Connecticut_ for you? Begged you to get clean, to come home? But it’s always about what Sam wants, isn’t it?!” 

Dean felt his temper rising, fists clenched. “When you left me with dad and ran away to that boarding school in the first place?”

“Dean, I—” Sam sputtered.

“No. I sure as hell don’t owe you anything,” Dean sighed. “I need more time.” 

Sam didn’t meet his eyes. “Okay. Yeah.” He swallowed and nodded to himself. “I get it, you need time to forgive me. But if I’ve learned _anything_ from how you sacrificed everything when I wouldn’t listen to you, it’s that this will never get any better if I’m giving one hundred percent and you don’t ever reciprocate.”

Dean sighed, feeling even more exhausted by the sound logic. 

“Okay Sammy, you’ve made your point. I can _try_. No guarantees.”

Sam smiled softly, suddenly looking very young. “That’s all I can ask for.”

“Well, I’m gonna call it a night now.” Dean escaped to his room down the hall and immediately collapsed onto the bed. 

~~~~~~~~

After school the next day, Dean was finishing up some shopping and errands for Henry when he spotted a familiar car. Smirking to himself, Dean walked over and leaned back on the front fender of Castiel’s Continental, right as Castiel happened to exit the convenience store. 

Time to try this again, then. Dean put on his most charming face and waited for Cas to approach. “Nice ride.” He made a point of sniffing the air. “Do I smell french fries?”

“Are you following me?” Castiel liked getting right to the point then.

“I was in the laundromat. I saw your car, thought I’d stop and say hello, that’s all.” he explained, hands held out in defense.

“Well, hello.” Cas moved to open the door, but Dean slid in front of it, blocking his hand. 

Dean tried again. “So, not a big talker then?” 

“Depends on the topic. Believe it or not, my biodiesel car doesn’t really whip me into a verbal frenzy.”

Dean crossed his arms and smiled. “You’re not afraid of me, are you?”

Castiel scoffed. “I’m not usually afraid of anyone I can easily outrun.”

“ _Most_ people seem to be.” Dean clarified, “Afraid of me.” Until recently, apparently. His encounter with Brady popped into his head and he frowned. He must be losing his touch. 

“Well, I’m not most people,” Cas said decisively, crossing his arms. 

“Well maybe you’re not afraid of me, but I’m sure you’ve pictured me naked, huh?” Dean winked.

“Am I really that transparent?” Cas bit back sarcastically. He forcibly shoved Dean off to the side and effectively pulled open the driver’s door. Dean sidestepped and watched him from the curb as he started up the car and began to back out of the spot, music blaring.

At the same time a familiar red Alfa Romeo squealed around the corner and stopped just shy of the Continental. Dean lifted his hand to his mouth and his eyes bugged when the driver jumped out and headed for the convenience store. It was the sucker, Brady. 

“Hey, do you _mind_?!” Cas protested to Brady’s retreating form. 

Without sparing a backwards glance Brady popped his gum and returned, “Nope, not at all.”

Cas’ face twisted with rage, and before Dean could say or do anything, Cas accelerated backwards right into Brady’s car, the shriek of metal gruesome. _Holy shit._ Brady turned around and stopped in his tracks past Dean, no doubt struck dumb by the damage to his douche-mobile. 

“You _asshole!_ You’re going to pay for this!”

Brady continued to screech towards an impressively unflustered Cas. Dean couldn’t hold back a grin as he witnessed the ordeal, but made a mental note never to piss Cas off. Dude looked downright homicidal when he was pissed. And also maybe really sexy. But mostly scary. 

Cas simply rolled his window down and made a show of glancing behind his car with affected disinterest. “Whoops,” he deadpanned over the din.

Dean’s smile grew even more. 

~~~~~~~~

“Whoops?! My insurance doesn’t cover ‘whoops’!” Jody exclaimed as she paced back and forth. 

Cas reclined on the couch, eyes not meeting Jody’s. “How about you just tell them I had a seizure.” 

“Cas, you don’t act out.” At his skeptical expression she added, “Destroying property isn’t your MO. Is this about Tufts? Are you upset that I want you to stay close to home?”

Cas sat upright. “Maybe I’m _upset_ that you’re just punishing me because you’re so paranoid they’ll find me again.”

“I never said anything about your—”

“Fine. We’ll just ignore the fact that I’m biologically related to a bunch of psychopaths. But I’m not some helpless kid anymore.”

“You’re in my charge; it’s my right to worry! Hell, it’s practically been my part-time job.”

“So what I want doesn’t matter?”

“Is it really so bad that I’m worried about your safety and wellbeing?”

“I want to have the free will to make my own choices and not live in constant fear of something that _might_ happen! And I want you to stop trying to control everything just because you couldn’t stop what happened back then!” Cas could feel tears starting to form but he forced them away. 

“Yeah, well, you know what I want?! I want to know that I’m doing everything I can to ensure that my kids are safe and—” Jody was cut off by the blaring ring of her pager. She looked at it and sighed. “There’s an emergency, I have to get to the station. We’ll continue this later, okay?”

Cas stormed out of the living room, desperate for the sanctuary of his bedroom at the end of a shitty day. Of course, he was intercepted by Jess stomping angrily towards him. 

“Did you just maim Brady’s car?!”

Cas shrugged. “Looks like you’ll have to take the bus again.” He shot her a fake smile. 

“Has the fact that you’re completely psycho managed to escape your attention?” she shrieked. 

“As you well know I come by it naturally!” Cas snapped back as he brushed past her up the stairs, leaving Jess calling for Jody in his wake. 

Cas slammed his door shut and flopped onto his bed, ignoring the copy of _A Single Man_. He closed his eyes and let his mind drift. Once he pushed away everything that was happening at home he was naturally left with thoughts of Dean. He chuckled. Between all these fights at home and finding time to keep up with volunteering, here he was, thinking about some _boy_. How cliché. 

Dean had come out of nowhere. Most of the time the boy didn’t even bother showing up to their English class and their paths never crossed otherwise. From what little he had gathered, on top of being some lazy delinquent student Dean was infuriating and self-absorbed. Those traits hardly set him apart from anyone else at Thompson. Why couldn’t Cas dismiss him as easily? His mind unhelpfully reminded himself with images of freckled cheeks, bright eyes, and spiky dirty blond hair. Underneath the oversized leather jacket, cigarettes, and deadbeat routine Dean Winchester was, simply, very beautiful. He couldn’t unsee it.

Cas groaned, smothering a pillow over his face. He hadn’t let himself think about anyone like this since the fallout with Brady and his subsequent transformation sophomore year. His masochistic mind conjured up the past and those secret flings, the uncertainty and the screaming exchanges.

There was a reason he’d sworn off dating until he was out of this hellhole, and he was going to stick to it. But it couldn’t hurt to linger a little on Winchester in his imagination, right?

~~~~~~~~

Dean slammed his locker shut, revealing an angry Brady glowering next to him. “When I shell out, I expect results,” he spat angrily.

“Yeah, yeah I’m on it,” Dean replied, irritated. He didn’t have time for Brady’s shit today. Henry’s hip was given him more trouble than ever. Convincing Castiel to even acknowledge him without hostility was proving to be a lot harder than he anticipated, which should turn him off of Brady’s stupid game. For some inexplicable reason it had him feeling the opposite. 

“Watching that jackass violate my car doesn’t count as a date.” 

Dean sighed. There was only one reason to keep this going, and seventy-five bucks wasn’t going to cut it. He cleared his throat. “I just upped my price.”

Brady turned. “What?” “Hundred bucks a date. In advance.”

“Forget it.” Brady was seething. 

Dean glared back. “Forget his sister, then.”

Dean once again watched the glacial turning of wheels in Brady’s mind, evaluating his new offer. Eventually he took out his wallet and pulled out two fifties. Dean took the money with a tight smile and took off to shop class. “I hope you’re as smooth as you think you are, Winchester!” Brady called out after him.

As he walked down the hallway, his thoughts settled on Cas. It wasn’t going to be easy to get through to him— the dude clearly hated him and probably everyone else at school. Dean chuckled internally, he could definitely understand why. 

Getting Cas to hear him out was only the first obstacle, but would also be the hardest. He could try and tell Cas the truth and offer to split the cash? It might give him some points if Cas knew he was doing this to help his grandfather, but no. It’d probably make him look worse. Dean already had an image problem with Cas, and Dean could see all of this backfiring. 

So honesty was out. He didn’t have much else to go on, he barely knew the guy. Clearly, his usual Roadhouse-tested charms wouldn’t work. Dean shook his head as he arrived at the shop room—he’d figure something out somehow. He gathered up his materials and prepared to get lost in his work. 

Dean was working on his project when he saw Sam and his redheaded friend walk into the classroom. _“Go.” “No, you go.” “I went last time.”_ Dean overheard their bickering and surmised that they were plotting to bug him again, or _worse,_ get him and Sam to have some sort of feelings fest. Dean wasn’t ready to reconnect with his brother and go toss the ball and have a picnic lunch at the park. It wasn’t that easy to forgive and forget.

He pretended not to notice as Sam started to make his way over to him. Dean figured he would brush them off same as before.

“I know what you’re trying to do. With Castiel,” Sam started, rattling his words out quickly like he knew Dean would interrupt him. 

Dean twisted to face his brother. “Is that right?” He smirked in an attempt to cover his surprise. If word of Brady’s scheme had already gotten out and a lowly pair of sophomores already knew about it, he was in trouble. This new virtuous Sam was probably here to talk him out of it. “And what exactly do you plan to do about it? Stop me?”

“Help you out, actually.” Sam’s face betrayed nothing but honesty.

“You and Carrot Top here? Why’s that?” Dean asked, genuinely curious. So much for virtuous.

The redhead chimed in, thrusting out her hand. It only shook a little. “Name’s Charlie, actually. The situation is that Sam here has a _major_ crush on Jessica Moore.”

Dean snorted. “What is it with this chick? Does she have beer-flavored nipples or something?”

“Hey!” 

Charlie put a quelling hand on Sam’s shoulder. “I think I speak correctly when I say that Sam’s love for Jess is more pure. Purer than, say, Tyson Brady’s.”

Dean raised his hands. “Look, not to bust up your little romcom dream but I’m just in this for the cash. Brady can plow whoever is dumb enough to want to.”

“Okay,” Sam sounded genuinely offended. “There will be no plowing. And Jess isn’t dumb! Why does everyone keep saying that?” Dean had to hold back a smile. It was all too easy to rile Sam up.

“Dean. I can call you Dean, right?” Charlie asked. “Let me explain something to you. You see, we set this whole thing up so that _Sam_ can get the girl. Brady’s just a pawn. He thinks I’m doing this for _popularity points._ ” She rolled her eyes.

Dean raised his brows as the pieces clicked into place. With Sam and his new buddy Charlie as the puppet masters, the whole charade just got more complicated. If Brady ever caught wind of the truth Sam could wind up in more hot water than ever. 

Hesitant, he asked, “So you two are gonna help me get close to the wild beast?” Neither of them looked up to the task when it came to someone as antagonistic as Castiel Novak.

Both Sam and Charlie grinned. “We’ll do some research, but let’s start here.” Charlie said and handed him a flyer. “Friday night. Dick Roman is having a party. It’s the perfect opportunity for you to take out Castiel.”

Dean resisted the urge to laugh. Cas? At a _high school party?_ “I’ll think about it.”

He stared them down until they turned to leave before setting back to his project. Anyone with some intelligence would recognize a lost cause for what it was and call it a day. Dean should give up on Cas, especially now that _Sam_ was involved, but he felt more motivated than ever. He shook his head, smiling. 

~~~~~~~~

Charlie and Sam exited the shop room, grinning at each other once they cleared the doorway. Charlie turned to Sam, excited for the next part of the plan for her own reasons. “And now, time for a little revenge.”

She looked down at the yellow flier in her hand. It read, _‘wine and cheese party, future MBAs only.’_ She crumpled it, and pulled out another from her bag. This one, however, read: _‘Party!’ ‘Free beer! Don’t call, just show up!’_ and listed Roman’s address. She smiled to herself. “This is going to be some party. Let’s do this.” She handed Sam a stack of fliers and they dumped them down the stairwell. They fluttered down like spring cherry blossoms and students snatched them from the air and the floor, the noise level rising with the student body’s excitement. 

Sam and Charlie high-fived.


	2. ACT II

Walking down the hallway, Jess smiled when she spotted Brady casually leaning on his open locker and he waved, beckoning her over. 

“Okay, so this is very important. Which one do you like better?” He held up two professional-looking photos of himself for her evaluation.

He wore identical expressions and Jess squinted between them, trying to spot any differences apart from the color of his shirt. She bit her lip. “Um, I think I like the white shirt better.”

He nodded his assent. “Yeah, it’s more–"

“...pensive?” she guessed.

Brady frowned. “Aw, damn, I was shooting for thoughtful.” He put the photos away and then folded his arms, facing her fully. “So, you going to Dick Roman’s thing on Friday?”

She brightened at the subject change. “Yeah, I might.”

“Good. ‘Cause I wouldn’t bother if you weren’t planning to show.” His smile was sly and Jess was sure his teeth twinkled with light like some Colgate commercial. On second thought, Brady probably _had_ shot a toothpaste commercial. 

Before she could reply, the bell rang and she gave him a coy parting smile before turning to walk away. From her peripheral vision she could’ve sworn she saw Brady wink at himself in the mirror on his locker. 

~~~~~~~~

“Okay, here she comes. Now go!”

Charlie shoved Sam into the stream of moving students and he stumbled before carving out a space to walk next to Jess down the hallway. 

“Hey, Jess!” He beamed at her and she answered with a polite if slightly confused smile. He cleared his throat, remembering his and Charlie’s plan. “So, have you heard about Dick Roman’s party?” 

Her smile morphed into a troubled pout, which was somehow no less charming. “Yes, of course I have. I really, _really_ want to go, but you already know I can’t. Not unless _Cas_ goes.”

He let out a heavy sigh. “Yeah I know, I’m actually working on that. You really weren’t exaggerating about him.” Surely Jess would be willing to give him some helpful hints? “So what kind of guy does Cas usually go for?”

“I don’t know. He’s kind of a misanthrope.” She frowned, pausing to think. “He hasn’t exactly been open about his dating life since coming out. What I do know, though, is that he’s said he’d rather die before dating a guy that smokes.”

It wasn’t much for a start, but was already a strike against Dean. “Anything else?”

She snorted. “You’re asking me to understand the inner-workings of my brother’s twisted mind?”

Sam chewed his lip. “Well, we need to figure _something_ out, if you want to go to that party.”

A mischievous look came across Jess’ face. “I think I might have an idea. Meet me after school,” she said before slipping into a classroom.

A warm feeling overcame Sam at the thought of visiting Jess at her _home._

Later that afternoon, they arrived at a small suburban home, and Jess showed him inside.

“No one’ll be home for at least an hour, so we have plenty of time.”

Raising his brows, Sam followed Jess as she grabbed his hand, spun around, and led him up the stairs. They entered what he assumed to be Cas’ room, and Jess moved immediately to the dresser and began rifling through the drawers. Interestingly, the drawers contained few clothes.

Unsure what to do with himself, Sam crossed his arms and stood, eyes cataloguing the crowded walls of posters and political banners. Clothes were strewn across the floor as well, piled up against the bed in what looked like a days-old load of clean laundry that never made it into the dresser or closet. He suppressed a grimace at the sight, unable to reconcile the scene before him with Dean’s meticulously neat living space. The door moved open and Sam jumped, spooked, until he looked down to see a dog streak past and jump up onto the bed. He curled up at the edge, staring up at Sam with brown eyes. 

Jess turned back to him, eyes landing on the dog. “Oh, that’s Leo.”

“Can I say hi?” Jess nodded and Sam smiled, running his hand softly through the silky fur behind the dog’s ears. His tail wagged lazily. 

Jess leaned back on the dresser, looking down at a collection of odds and ends in her arms. “Okay. So we have class schedule, reading list, a bunch of receipts, concert tickets...ooh, report card, and this ‘ _Save the Bees’_ pamphlet.” 

Sam nodded along, taking the stack of papers. “This is a good start. It gives my guy something to work with.”

Jess’ eyes widened in interest. “Your guy? You mean you already found someone?”

“Well,” Sam swallowed and shifted the papers nervously. “I just meant ‘guy’ as in, you know—”

“Right, sorry, getting ahead of myself. I’ll let you do your thing.” She searched his face. “You do think you can do this still, right?”

Sam nodded profusely. “Yeah, yeah! I mean, I’m really close. No need to worry, I’ll be seeing you at that party. Promise.”

~~~~~~~~

Dean was enjoying a cold beer and game of pool at the Roadhouse when he spotted Sammy and Charlie entering. They shuffled towards him, eyeing the bar uneasily. The bartender caught Dean’s eye, looking between him and the newcomers, and shook her head with a smile. Dean returned the expression, shrugging, before turning his attention to the interlopers. 

“So what’ve you got for me?” Dean held out a hand as if expecting an executive report summary. 

Sam perked up. “A little insight into a very, uh, complicated guy.”

Charlie, who was looking at Dean strangely, squeaked out, “Should you be drinking alcohol when you don’t have a liver?”

“What?!” he and Sam exclaimed at the same time. 

She shook her head rapidly. “Nothing, nothing. Never mind.”

Sam cleared his throat. “Okay, so first thing, Cas isn’t a fan of smokers.” 

Dean scowled. “So, you’re telling me I’m a ‘ _non-smoker’_ now?” he spat out. 

“Man up, Dean. It’s just for a little bit.” Sam continued, “There’s another thing. We found this pamphlet. He’s real big on animal rights, keeps a vegan diet.”

Dean’s jaw fell in horror. “Let me get this clear. I can’t eat _meat_ now either?”

Charlie winced, interjecting, “Actually, it’s more than that. No meat, no fish, no dairy, no eggs—”

“What the hell is _left_?”’

“Fruit and vegetables?” Charlie frowned.

“Moving on,” Sam trailed off, shoving his hand into his pocket and digging for a list. “Okay, so his likes include LGBT literature, running,” 

Dean made a gagging motion.

Sam glared but continued without pausing, “and ‘queercore.’ We guessed that’s a music thing. And possibly bees, but we’re not exactly sure about that one.” He turned over the list and handed it to his brother. “On the back there’s a list of CDs he has in his room.”

Dean looked over the list and scoffed. “What am I supposed to do with all this? Buy this guy a salad and a book and then sit around listening to angry gay punks who can’t sing?”

“Have you ever been to _Homo-A-Go-Go_?” Charlie asked. 

Sam clarified, “His favorite band is playing there tomorrow.”

Dean looked pained. “No. No way. I can’t be seen at _Homo-A-Go-Go_.”

Sam looked up at Dean with his pleading expression. “But Cas’ll be there, he has tickets.” Damn it, he couldn’t resist the puppy dog eyes.

Charlie added, “Just assail your ears for one night.”

Dean groaned, rubbing a hand down his face and nodding. This was for Henry’s therapy; he’d suffer through a lot of things for that. He ignored the triumphant looks on their faces as they sped out of the bar and shook his head at their enthusiastic high-five. He was feeling decidedly less optimistic about the whole thing. Even worse, his beer was warm. 

~~~~~~~~

After presenting his fake ID to a skeptical yet disinterested bouncer at the door, Dean reluctantly followed a path of glitter to get to the crowded main area of the venue, immediately taking a seat at the bar.

“Winchester!” the bartender laughed. “What are you doing here tonight?”

“Benny! Long time no see, man!” He smiled. “Thought I’d check out the dating pool here,” Dean joked, nervous energy dissipating.

Dean looked over his shoulder out towards the dancefloor. Castiel stood out to him immediately; his hair was artfully untamed and he wore a tight black t-shirt and ripped jeans that were hugging all the right places. Most startling of all was the serene smile he wore in place of his trademark scowl. He danced closely with a tall girl dressed in a flowy white dress, who he guessed from Sam and Charlie’s debriefing was Cas’ sole friend Gilda. Dean made small-talk with Benny for the rest of the song, sipping slowly at his drink and shrugging off any stray gazes or hands. His ears picked up a familiar deep, gravelly voice and Dean held his breath. 

“Two waters, please.” Cas said, breathing hard.

Out of the corner of his eye, Dean caught Cas’ sideways glance. Surprised recognition morphed into displeasure and Dean brought his glass back to his lips to hide his smirk, keeping his gaze fixed on Benny while he made up drinks.

“What is this, another ambush?” 

Dean pretended to not hear him, lightly bobbing his head to the music. 

Louder, Cas asked, “Well? Why are you stalking me, Winchester?”

Momentarily thrown off-balance by the use of his last name, Dean recovered quickly and frowned, cracking an eye open towards the other guy. “Do you mind? You’re kinda ruining this for me.” He waved indistinctly in the air.

Cas narrowed his eyes, radiating hostility. “You’re not surrounded by the usual cloud of fumes.”

“I quit.” Dean shrugged. “Apparently smoking kills.”

“Really?” His scrutiny gave way to genuine surprise. 

Dean smiled to himself, silently thanking Sammy for the tip.

“Well, I better head out before I miss _Smells Like Queer Spirit_. It’s pretty exciting to see Freeman back in his hometown.” Flicking down a few bills from his wallet and winking at Benny, he abruptly stood up and headed into the crowd, leaving Cas gaping behind him. Internally he counted, _one, two . . ._

“No way do you listen to Pansy Division,” Cas called out decisively.

“Surprised?” He cleared his throat, turning around. Cas had snatched his waters from the counter and was trailing behind Dean. “You know, I was watching you out there before and you’ve got some pretty sexy moves.” Cas looked more confounded than ever, so Dean pressed in earnest, “Come to Roman’s party with me.”

Cas tilted his head, calculating. “You don’t take rejection too well, do you?”

Dean sucked in a breath. “Is that what this is? You’re rejecting me?” Not for the first time, he wished he’d gotten the genetics for the puppy dog pout instead of Sam.

Cas didn’t answer immediately, so Dean clasped his hands around Cas’ shoulders and pleaded, “Just one date. If I’m as bad as you seem to think, just kick me to the curb. I won’t even ask for my jacket back.” He fought the urge to wink, wagering that it would do more harm than good with this guy.

Cas’ mouth quirked, an almost-smile.

“Is that a yes?” Dean tried.

“No.” Cas stared over Dean’s shoulder towards the stage, stubborn.

Dean’s brow furrowed. “So, was that a no?” 

Cas looked at him sidelong now, smirking. “No.” He shrugged off Dean’s hands, which were still clutching at his shoulders, and pushed past him to rejoin Gilda.

“I’ll see you at nine!” Dean hollered after him. 

Dean smiled to himself as he walked back to the bar to chat with Benny a little longer. He’d never admit it to anyone, but the thought of beautiful blue eyes stayed with him the rest of the night. 

~~~~~~~~

On Friday, Cas was once again reading on the couch, Leo stretched out on Cas’ feet fast asleep, when he heard creaking as presumably Jess and her equally-vapid friend Rhonda came down the stairs. When it came to decades-old wooden staircases versus teenagers tiptoeing, the staircase was always the winner. Naturally, this was followed by the unmistakable sound of Jody clearing her throat in the hallway. 

“And where are you two heading?” she asked knowingly, her casual tone fooling no one. 

“Well, if you must know, it’s just a small party with friends.” Jess’ voice dripped with innocence.

Cas looked up from his book to catch Jody’s exaggerated appraisal of the girls’ outfits and makeup. He snorted.

Rhonda pleaded, “C’mon Sheriff Mills, it’s just a party.”

Jody scoffed. “Yeah. And hell is just a sauna.”

Cas admitted defeat after reading the same sentence six times, setting his book spine-up on the ground beside the couch. He slowly extracted his legs out from behind Leo, who shot him a look of betrayal at the change in position. He made his way over to the hallway, stretching out his arms over his head and eventually settling to lean against the wall, arms crossed. 

Jody looked to him. “You know anything about a party?” Cas yawned and shrugged, feigning ignorance. “Sorry Jess, you know the rules, if Cas isn’t going, neither are you.” The sheriff squeezed Jess’ shoulder before sweeping past into the kitchen, closely followed by the dog.

Jess groaned and faced towards Cas. “Can’t you just be normal one time in your life?”

Cas fought the urge to roll his eyes. He’d had more than his fair share of ‘normal’ while at Thompson and had resolved never to go back. It made his skin crawl to dwell on memories of high school parties, fake friends and fake laughter, of _Tyson Brady._ He had the power to ensure that Jess would be spared that particular pain, at least for his last few months there.

Cas took a breath and replied, “This party is a lame excuse for the idiots at our school to drink beer and rub up against each other in hopes of distracting themselves from the pathetic emptiness of their—”

Familiar with his tirades, Jess and Rhonda recited with him in bored voices, “—meaningless, consumer-driven lives.”

Cas balked. Jess pleaded, “Cas, will you please just do this for me, just this once?” Apparently she had already jumped to bargaining. She glanced toward the kitchen, where Jody was tossing slices of lunchmeat to Leo next to the sink. Her voice lowered and she hissed, “I know you went to _Homo-A-Go-Go_ last night, and I didn’t say anything. So please, do this for me.”

Cas bristled. “I don’t _owe_ you anything.”

Intending to take his leave and retreat to his room, Cas caught the expression on Rhonda’s face. She was antsy, eyeing the door, likely planning her own retreat. Probably planning to ditch Jess for the party. If Jess was desperate enough to beg him, she might make a break for it later too. As much as he loved the idea of gloating when she inevitably got caught by Jody, a smaller voice in his head reminded him that if he was at the party, there was a chance he could help keep her out of Tyson Brady-related trouble. Plus, there was still the matter of Dean Winchester that he’d been desperately trying not to think about. 

He threw his head back and groaned. “Fine, fine. You win. _This time._ ” Jess and Rhonda squealed and ran up to envelop him in a big hug. What had he just gotten himself into?

Cas looked down at his clothes, smoothing out the wrinkles in his shirt. No way was he going to any trouble for the people at this party, much less Winchester. He grabbed his jacket and keys and opened the front door, only to find none other than Dean Winchester himself, hands in his pockets, standing on the stoop. His eyes were wide like he’d been caught in a crime. The look was replaced with a grin. Cas narrowed his eyes and asked, “What are you doing here?”

“Nine o’clock, right?” Cas blinked. “I am a _little_ early, though,” Dean added, biting his lip. 

Cas brushed past him out the door and jogged down the steps. “Fine. But I’m driving.” He jingled his keys with his wrist over his shoulder. 

~~~~~~~~

Once he rounded the corner onto Dick Roman’s street, Cas pulled into the first available slot, marveling at the crowd of cars and energized teens. Music burst from Roman’s house, though the more appropriate term was mansion, each time the front door swung open to admit more people. 

Dean fell into step with Cas. “Jeez, cops’re bound to shut this down any minute. It’s crazy in here.” 

Cas silently agreed as he took note of the already-drunk teens making out along the walls inside, as well as the bottles of alcohol being freely passed around. Jody was off-duty but there was no doubt she would hear about the hundreds of rich, underage Thompson kids at a party of this magnitude. Tamping down on his general unease, Cas made a beeline for the staircase, hoping it would be less crowded on the second level. The friction of so many bodies moving in a mass had the house feeling like a sweat lodge and Cas shrugged out of his jacket, regretting the extra layer.

He was half-aware of Dean struggling to keep up with him. He tried to suppress the feeling of guilt that bubbled up, but paused at the top of the staircase just in time to see a girl throw herself into Dean’s arms, exclaiming “kiss me!” Cas held back a chuckle at Dean’s shocked face as he peeled the girl off of him and into the arms of another guy leaning on the banister. “Kiss _him_!” he shouted over the music. 

Cas had already headed back down the stairs after encountering a row of closed doors in the upstairs hallway. It didn’t take a rocket scientist to guess at what he’d find on the other side of any of those. In the dining room, Cas found the last beer in a six-pack and pried off the lid on the edge of what was likely a ten-thousand dollar dining hutch. Tipping back the drink, he flinched when he heard the voice of the last person he wanted to see. 

“Hey! Who invited the fruit loop?” 

As usual, Cas let the insult roll off him and instead affected an expression of concern, wide eyes zeroing in on Brady’s forehead. “Is that a bald spot?”

Brady’s smug expression melted into one of terror as he clapped a hand to his head, patting gently around the edges of his hair. Cas closed his eyes briefly, wondering how his peer had advanced to the twelfth grade when he lacked even the most basic critical reasoning skills. Not for the first time, he lamented the state of the American public education system. 

Cas turned away, more than ready to put space between him and the human embodiment of a migraine, but Brady called after him, “Hey!” and blocked his path. His eyes flicked up and down Cas and he asked, “Seen your sister around?” Brady crowded closer to him, whispering in his ear. “Or have you been missing our time together?”

Cas’ nostrils flared and he pushed Brady away. “Find someone else to fawn over your headshots and leave Jess alone.”

Brady raised his palms defensively as he retreated. “Hey, I’ll keep my distance from your sister. But I can’t guarantee _she’ll_ stay away from _me._ ” 

Cas took a deep breath to steady himself. He couldn’t let Brady get to him. 

~~~~~~~~

Charlie basked in her own schadenfreude as she watched Dick Roman yelling in circles, voice hoarse, after a pair of wide receivers playing catch with an expensive-looking vase and knocking over all the furniture in their wake. So far her revenge plan had exceeded all expectations.

She leaned back into her seat, a nice velvet settee, observing her peers like a circus act. Her grin widened as two other jocks started beating the crap out of each other, when she felt the cushion dip as someone slid next to her. She looked over to see none other than Castiel’s best friend Gilda, and almost jumped out of her seat. 

“I know what you did here,” Gilda said knowingly, head tilted to cast her long hair like a veil. Charlie paled. Were they already onto her and Sam?! 

“I _really_ hate Dick,” Gilda continued, winking at her double-entendre. 

“Oh . . . OH, you—” Charlie blushed, but laughed along with Gilda. “The pleasure’s all mine.” Charlie half-bowed in her seat, until she realized what she was doing. She blushed even harder, feeling completely foolish and out of her element. She cringed internally at herself. What was _wrong_ with her right now? 

Gilda smiled warmly. “I don’t believe we’ve been formally introduced,” she said, holding out a slender hand. “Gilda.”

Charlie somehow managed to find her voice as she took Gilda’s hand in hers. “Charlie.” 

~~~~~~~~

“Hey, Novak! Look who found me!” For emphasis, Brady squeezed Jess’ shoulder and pulled her in close. Cas shot him a searing glare and opened his mouth to retort before looking to Jess who shook her head minutely, eyes wide. 

He sucked in a breath and addressed her. “You can’t do this, not with him.” 

“We’re doing this here? Really?”

“Jess, stop. There’s something I need to tell you.”

“Save it, Cas. If I wanted a lecture I’d go ask the World Champion of them back at home.” Voice pitching higher, she implored, “Can’t you just go and have some fun? I just want to have funlike a _normal_ teenager for once in my life.” She tugged at Brady. “Let’s go.”

“Bye-bye!” Brady sneered, smirking.

Cas was seething. He tossed away his useless, empty beer and absently noted that his jacket had disappeared. As his irritation mounted, Cas turned to see someone tipping up a bottle of tequila towards their lips and plucked the handle right from their hands. Ignoring their slurred protest, he took a long pull right as he felt someone land a warm hand on his shoulder. 

“Whoa, what’s this?” Dean’s eyes widened at the Jose Cuervo in Cas’ hands. “I’ve been looking all over for you.”

“This?” Cas gestured around them. “We’re at a party full of underage, hormone-riddled high school students on a Friday night that magically _hasn’t_ summoned every cop in a twenty mile radius. Aren’t I supposed to be getting wasted?” 

Dean frowned and shrugged. “I dunno. I say, do what you wanna do.”

“Looks like you’re the only one.” Cas lingered on Dean’s earnest expression before barking out a laugh. “See ya.” He shouldered his way into the crowd, taking another cavalier pull right from the bottle as he went. If he had to endure this thing he sure as hell wouldn’t be doing it _sober._

Time seemed to pass quickly as he drifted from room to room, bottle paradoxically growing heavier in his hands until he lifted it to his lips, empty. Frowning, he let it clatter to the floor. The liquor had done its job splendidly—despite the blaring music and raucous partygoers Cas’ mind was serene and bubbly. His eyes tried to focus on flashes of teeth, waving hands, and bodies moving with the beat. It was harder and harder to remember why he hated these so much. He began swaying to a particularly catchy Backstreet Boys song when someone pulled the bottle—it was now unaccountably some kind of alcopop—out of his hands. 

“Hey! Hey! How about you let me have some of that?” Oh, Dean had found him again. He reached forward to grab for the bottle.

“Knock it off, Dean. This one is _mine_.” 

Dean raised his brows. “I think you’ve had enough.” He turned the label to face him, wrinkling his nose. “What is this crap anyway? ‘ _Hooper’s Hooch_?’”

Cas stormed. “Cutting me off? S’not attractive.”

He stomped away, hands landing on shoulders until he made his way into another room. He blinked and swayed to a stop, watching a group of drunk jocks crowded around a keg, cheering. He marched up to them and emphatically announced, “I’m next.” The group cheered again at this turn of events and Cas didn’t bother reminding them all how much they were supposed to despise him. Inebriation certainly had its perks. Before he knew it, he was being hoisted up and chugging beer. More partygoers had entered the room and the cheers grew louder. 

All of a sudden, the chanting died down and he was being placed back on the ground with something else supporting his weight. He swayed and his vision was blurry, but he pushed the arms away. He could walk on his own, thank you very much. He heard a deep, rumbling voice that sounded familiar right as he felt himself tripping and everything turned black. 

Green. 

Quiet. 

The first two thoughts he had as he opened his eyes and his vision adjusted. He blinked a few times to see Dean crouched in front of him. 

“Welcome back.” Dean smiled. “How’re you feeling?”

Cas felt his head throbbing, but he looked away, embarrassed. “I’m fine. Where’d everyone go?”

“I chased your fans away. And no, you’re not fine.”

“Really, I am fine,” he insisted. “I just need to lie down for a little bit.”

“No way, if you lie down you’ll fall asleep.”

“Sleep is good,” he said with a small smile. 

“Not if you have a concussion. C’mon, let’s get you some air,” Dean reached out a hand again.

Cas reluctantly accepted, and followed Dean outside. There was a bench in a relatively quiet and dark corner of the backyard. Dean arranged him on the seat before sliding in next to him. If not for the alcohol, the stone bench probably would have felt uncomfortably cold.

A lanky guy emerged from the light of the house and approached them. “Dean I need to talk to you,” he insisted. 

“I’m a little busy right now, Sammy.”

The guy, Sammy, must have communicated something important nonverbally, because Dean sighed and looked at Cas, reluctant to leave. “Okay. Cas? Listen. Stay right here, try to stay awake. I’ll be right back. Five minutes, tops.”

Cas attempted to nod, but ended up dropping his head between his knees.

Dean looked back to Sam, standing up. “Better make it two.”

~~~~~~~~

Sam led Dean a few paces next to the side of the house, where a few stragglers were attempting to light cigarettes. Dean spared them one longing glance before looking back towards Cas to make sure the guy hadn’t fallen down or passed out.

Sam spoke, radiating irritation. “The whole thing is off.”

“I’m sorry, what?”

“I said it’s off, Dean. She never wanted me. She just wanted Brady the whole time.” Sam exhaled in frustration. “She’s made it pretty clear by avoiding me all night and practically hanging off that jerk’s arm.” He gestured dully towards Cas. “Sorry for setting you up to deal with all of that.”

Dean frowned. “Cas? No, don’t worry about him. We’re fine.” He searched Sam’s downturned face, contorted with hurt, anger, and resignation. Dean had never seen the kid so heartbroken, not even after everything that happened with Ruby. “Listen, do you like this girl? _Really_ like her?”

Sam nodded. 

“And was she worth all this trouble?”

“I _thought_ she was, but maybe after Ruby my judgement is sti—”

Dean cut him off by placing a hand on Sam’s shoulder. Things were still rocky between them, but he couldn’t stand to see Sam so unsure of himself. 

“Listen, she either is or she isn’t. First of all, that meathead, Brady? He’s not half the man you are. And second, don’t let anyone, not even you, ever make you feel like you don’t deserve love and happiness just like anyone else. I say you go for it!”

He heard a thud, and turned back to see Cas fall to the ground against the bench. Dean rushed over to him, helping him up from his armpits. The guy’s face was totally flushed and his eyes glassy. He was shivering too, the hair on his bare arms raised.

“You need any help here?” Sam had followed Dean and was looking Cas up and down with a grimace. “He doesn’t look too good.”

Dean pursed his lips. “Here, support his weight for me.” Dean helped guide Sam into position and then shrugged out of his leather jacket and draped it over Cas’ shoulders. “I’m gonna get him out of here. You should probably think about doing the same.” 

Together, they watched as a girl who looked more like an eleven year old than a high schooler ran out of the house and bent over a planter, hurling. Sam covered his mouth with his hand. “Oh, that’s disgusting. Noted.”

A thought occurred to Dean and dread crept up his spine. “Hey Sam? Can you check his pockets? For keys?” If Cas had left those in his jacket pocket he could be in for a hell of a night.

Sam heaved a sigh, but complied. He lifted Dean’s jacket and said, “Uh, looks like a wallet in right pocket, lumpy bulge in the left. Could be keys.”

Dean shifted a groaning Cas so that he was more stable, then warned him, “Okay Cas, I swear to God this isn’t a come-on. I’m just . . .” He bent his knees and felt Cas’ jeans for the left pocket, then extracted a set of keys. “Gotcha!”

Sam saluted Dean before heading back towards the party, and Dean steered Cas in the opposite direction towards the expanse of lawn leading up to a street lined with cars.

~~~~~~~~

“You are _exceedingly_ patronizing,” Cas huffed, increasingly aware of his position. 

Dean chuckled in return. “Seriously? Of course you’d still use big words while plastered.”

He wasn’t _that_ drunk. He pushed Dean’s arms off him to prove this point. He made it about two steps before beginning to sway and lose his balance, but much to his dismay Dean grabbed him just in time. He grudgingly allowed Dean to hold him up as they continued. 

“Why’re you doing this?” Cas asked. 

“I’m getting us out of there before your mom rolls up with the cavalry, guns blazing.” Dean felt Cas tense and looked over to see his eyes wide in alarm. “Kidding,” Dean said. “I told you, you have a concussion.”

“Like you’d care if I didn’t wake up.” Cas scoffed.

Dean grinned and pulled him closer. “Sure I would.”

“But why?”

“Well, if you kicked the bucket I’d have to start taking out people who actually like me.”

“Like you could find one,” Cas added playfully. 

“And who needs affection when I have blind hatred?” Dean retorted. 

“I don’t hate you,” Cas protested, before he tripped on the slick grass.

“What was that?” There was a hint of a smile in Dean’s otherwise innocent-voice.

“Uh, let me sit down a second.” Luckily there was a playground a few paces away and Cas managed to shuffle over to a swing set, still embarrassed at his earlier admission. He brushed away the settled water droplets and sat on the swing, shooting Dean a satisfied grin before abruptly falling over backwards. 

“Whoa there!” Just in time, Dean caught him in his arms, propping him back up on the swing. 

Dean took the swing next to him and started swaying slowly. “So, why’d you let him get to you?”

Cas stared at his shoes, which glistened with moisture. “Let who get to me?”

“Brady.”

“I hate him,” Cas deadpanned. Wasn’t that obvious?

“Well, you really showed him, mainlining tequila and doing keg stands.”

“Well, you know what they say.” 

“No,” Dean grinned. “What do you they say?”

Somewhere, Cas had a retort ready, but just then closing his eyes to sleep sounded like a much better use of his time. His lids slipped shut and he leaned on the chain of the swing, thinking about cozy leather jackets and green eyes and playful smiles. His brief reverie was interrupted by Dean, kneeling in front of him, shaking him awake. 

Cas lifted his head to face him, only inches away. “Your eyes have so much green in them.” He gave Dean a dopey smile, leaning forward. Then he promptly threw up at Dean’s feet. 

~~~~~~~~

Jess fidgeted with her jewelry as she and Rhonda waited in front of Dick’s house. All around them people were soaked in beer and sweat and yelling loudly, even though the music had been shut off for at least ten minutes. Jess was tired of shrugging off groping hands and listening to Tyson Brady droning on about his favorite subject—himself—all night long. And if she had to watch him do _one_ more modeling pose . . . 

She rubbed circles into her temple, feeling a headache coming on that had nothing to do with alcohol. How could someone so boring and self-centered be so popular, just because they were cute? She bit her lip. “I don’t know if we should go,” she whispered to her friend.

Brady chose her moment of doubt to strut up to them. “So we’re all going to Raph’s house. You guys ready?”

She pretended to check her watch. “Well, I actually have to be home in twenty minutes.”

“I don’t have to be home until two, so . . .” Rhonda trailed off, ignoring Jess’ stare.

Brady turned back towards her. “One more chance?”

“Oh no. I can’t. Damn.” Jess could detect the insincerity in her own voice but couldn’t muster up the energy to care. 

“That’s a shame, it really is,” Rhonda said, sounding equally sincere as she sidled up to Brady. “Well?”

He shrugged at Jess and smirked. “Let’s get out of here then.”

“Rhonda!” Jess hissed, offended at her friend’s betrayal. 

“You passed,” Rhonda shrugged, unremorseful, then hopped into Brady’s car.

 _Bitch_ , Jess thought to herself as she leaned back on the fence. She was getting colder by the minute, head pounding, and now without a ride home. From the last time she saw Cas, relying on him for a ride was clearly a no-go. Besides, even if he wasn’t passed out somewhere she had no desire to face his smugness once he found out how things with Brady had turned out. She crossed her arms miserably and weighed her options, interrupted by the sound of someone clearing their throat. 

“Have fun tonight?” Jess looked up to see the form of Sam. He wouldn’t meet her eyes. Dodging and pushing him off onto other girls all night to tag along with Brady hadn’t been her shining moment. 

“Tons,” she said sarcastically.

Sam shook his head and turned to walk away, but she reached out to stop him. “Wait, Sam?” He looked at her expectantly. “Do you have a ride? My head is killing me and I just wanna crash at home. Could you please help me find a lift?”

He frowned, looking put out, but admitted, “I’ve actually got a car here, my grandpa lent it to me for the night. You can hitch a ride with me, I haven’t had a drop to drink all night.” He started to walk towards the car and she followed after him. 

He drove in tense silence, which, to be fair, she deserved. She only piped up to tell him when to turn onto streets. As they pulled up to Jody’s house and came to a stop, he stared straight ahead and abruptly blurted, “You never wanted to go sailing did you?”

“Yes, I did,” she lied.

Sam snorted. “No, you didn’t.”

“Okay, well not _actually_.”

Sam finally turned to face her. “You know, that’s all you had to say.” He sighed. “Have you always been this selfish?”

Jess wanted to melt into the car seat. Or set it on fire. “Yes,” she whispered, sniffing.

“Just because you’re beautiful doesn’t mean you can do whatever you want and use people! I really liked you, and I defended you when people called you conceited!” He exhaled sharply. “I thought we were at least friends, and then you just blew me off . . .” 

Jess began shaking her head, a humorless smile growing on her face and Sam trailed off, mystified.

“Oh, shut up. You’re so full of shit.”

Sam tensed.

Jess faced him, expression twisted in anguish. “You don’t even know me! How are you any different from the guys who just want to get in my pants? What, just because you take me on some stupid boat first? You know more about my _brother_ than you do about me.”

Sam swallowed, staring forward.

“You were so intent on dating me you never even bothered _trying_ to be my friend.” Jess gulped, deflating. “I guess I could have tried harder to be your friend too. I saw you first as a means to an end, which isn’t fair either.” When had she gotten so comfortable with using people?

“Maybe you’re right,” Sam admitted. “I got so caught up in it all, and you’re just so . . .” He waved his hand up and down. “You know. I should’ve taken the time to get to know you first.”

Jess wiped at her eyes. “Looks like we both suck, huh?”

“We could always start over.”

Jess nodded. “Yeah, why not?” She held out her hand. “I’m Jessica Moore.”

Sam took her hand lightly. “Sam Winchester.”

“Friends?”

“Friends,” Sam nodded in agreement. 

Jess pecked him on the cheek as she got out of the car. “I’ll see you around then, Sam. Thanks for the ride home.”

~~~~~~~~

Cas sat in the passenger seat of the Continental, clutching at his half-empty water bottle and curled up with his left shoulder against the seat, watching as Dean drove around with ease. The rain had picked up, and the wet windows rendered the glowing signs and streetlights outside abstract and pretty, painting his driver’s face in a wash of neon reds and blues. Without his leather jacket, Cas could linger on his strong arms and the curve of his wrist on the steering wheel. Rather than feeling irritation at the commandeering of his car, Cas found that he didn’t mind the view at all. 

Dean must have become aware of his staring, because he cleared his throat and glanced over at Cas. “I thought you’d appreciate having a little time to sober up before heading home. It probably wouldn’t earn you any brownie points if I had to carry you over my shoulder to the front door.”

Other than a faint buzzing all over, the feeling had returned to his limbs and his eyes could focus again, so it looked like that plan had worked, mostly. He took another swig of water for good measure. Cas looked at the clock in the dashboard and winced. ‘Late’ was an understatement. His eyes lowered to the radio and he noticed for the first time the music playing from his cassette.

“I should do this!” he exclaimed.

Dean’s eyes widened at his outburst. “Do what?”

“This!” Cas emphatically pointed towards the radio.

“What, start a band?”

“No, install car radios,” Cas deadpanned, rolling his eyes. “ _Of course_ start a band. Jody would love that.” Dean pulled to a stop and Cas was surprised to see they had arrived on his street. 

Dean took off his seatbelt and twisted towards Cas, arm leaning against the back of his headrest. “Well, you don’t strike me as the kind of guy to ask for anyone’s permission.”

Cas’ heart beat faster. “So, you spend a few hours with me and think you know ‘the kind of guy’ I am?” 

Despite Cas’ reply, Dean’s face remained earnest. “Getting there. Or at least I’m tryin’.”

It might have been the alcohol or the possible concussion or the fact that Dean had sacrificed his whole night to drive him home, but Cas let his walls come down. He chose his next words more carefully. 

“The only thing people know about me is that I’m gay and ‘scary,’” he admitted.

Dean’s eyes twinkled and he smiled. “I’m sure you’ve heard I’m no picnic myself.” 

They gazed at each other, drawn close by the creeping cold now that the car and its heater was shut off. Cas couldn’t remember the last time he had ever been so open or felt so connected with someone. 

“So what’s up with your foster mom? Is she really a pain in the ass?” Dean broke the silence, gesturing up the driveway towards his house.

“No. Well, yeah.’ Cas briefly reflected on his and Jess’ situation. “It’s . . . complicated?” Cas wrinkled his nose at his own words. “She’s been nothing but accepting and caring all these years. But she worries, and it’s not all unfounded. But sometimes she just . . . wants me to be someone I not.”

“Who does she want you to be?”

“Like her? Or at least more like Jess, I suppose.”

“Ah. No offense to your sister, I know everyone digs her, but she’s . . . without.”

Cas couldn’t hold back his smile, and looked down at his lap. “Well, you’re not as vile as I thought you were.” 

Despite the traces of alcohol, Cas felt confident he wanted to explore this thing, this bond with Dean. He hadn’t forgotten his self-imposed rules in place for self-preservation, but none of them seemed to apply to Dean. It’d been so long since he had permitted himself feelings like this, and they were absolutely heady.

He raised his head to meet Dean’s gaze and got lost in the endless green, before wandering down to take in his beautiful freckles and finally settle on perfect lips. Closing his eyes, he leaned in, sensing the hitch in their shared breaths before closing the distance between them. It took a moment before Dean kissed back, and then Castiel was melting into the kiss, heart pounding. His hands cupped Dean’s face and he sighed into the kiss, sensing as Dean brought his arm around to curl fingers into his hair at the back of his neck. It just felt so _right_. 

He broke the kiss, only to slide over the seat to straddle Dean’s lap. It was a tight squeeze, and Dean grunted as they adjusted position. Cas dove back in, holding onto Dean’s shoulders as he continued exploring Dean’s mouth. As the kiss grew more heated, his hands roved over Dean’s chest and slid down to the hem of Dean’s shirt, sliding it up. Dean suddenly pulled away. 

“Maybe we should do this another time,” Dean said, out of breath, while smoothing his hands down Cas’ sides. He wouldn’t meet Cas’ eyes.

Cas paled.

This was humiliating. He needed to get away immediately.

In a panicked blur, he clambered off Dean’s lap and scrambled for the door handle, barely managing to slam the door shut behind him as he fled up the driveway, not caring that Dean called after him from the car or that he had the keys. He opened the front door of the house, thanking God it was still unlocked until he saw Jody waiting expectantly on the couch, Jess hugging her knees beside her. He closed his eyes, breathing hard.

~~~~~~~~

“Christ, Leo, it’s just me.” Cas kneeled and grabbed the barking dog by the ruff, letting him sniff his hand, like entering a code into a tripped security alarm. Satisfied, Leo quieted down and retreated to the couch. Cas reluctantly faced his foster mom.

“Dog probably doesn’t recognize the jacket.” Jody was pointedly looking at Dean’s big leather jacket, which Cas still wore. Her voice was dangerously calm, as if she were asking about soccer practice. “Where’ve you been?”

As if she couldn’t tell. “On a bender," he grumbled. Jess looked up, brows shooting up.

From the coffee table, Jody grabbed a familiar flyer and held it upright. Cas winced at the crumpled paper. “Found this hanging out of your sister’s backpack. This is the ‘small party with friends’ you two were referring to?”

Cas nodded slowly.

“C’mere, then.” Cas made a point of walking over to the couch in a straight line as nonchalantly as possible. Jody stood, plucking a small device from the table. Cas refused to meet her eyes. He heard a beep. “You know the drill. Blow as long as you can.”

Cas gaped, looking to his sister. Jess merely stared back with an expression somewhere between pity and fear. “I don’t think th—”

“I _strongly_ suggest you blow into this tube.” Cas heaved a sigh, briefly considering resistance. Jody killing him on the spot wouldn’t even be the worst thing to happen that night. Instead, Cas blew and the breathalyzer beeped. Jody looked at the reading, then scoffed. “Point-eleven. _Well_ past legally intoxicated. And you stink of beer and—”

Cas closed his eyes, remembering when he got sick. All over Dean’s _shoes._

Jody set the device down, crossing her arms. “Did you drive home?”

Cas frowned, shaking his head profusely, which he regretted immediately. “Of course not, I’m not a moron. De—a friend drove my car home.”

Jody pinched the sleeve of his jacket. “This _friend_ lend you the jacket, too?”

Cas shrugged, dropping down onto the couch next to Jess. She looked about as miserable to be there as he felt. Jody rounded on them and Cas braced himself for what was probably going to be an _epic_ lecture. He almost wished he was still drunk enough to drown it out. 

Sure enough, Jody raised her cop-voice and spoke. "Based on the way you’re both sitting there like you’re bracing for executions, I bet you both think I’m about to give some harrowing lecture. Honestly? I don’t see the point. I won’t waste my breath telling you how stupid and irresponsible you’ve both been. Or how disappointed I am. Instead, how about you two geniuses tell _me_ what I’m supposed to do with you.”

Jess whimpered, “Please don’t arrest us Jody.” Cas spun his head to glare at her. Jess added hastily, “You could ground us? I mean, you already saw that I didn’t drink a thing. Cas didn’t drive the car—”

Jody held up a hand to interrupt her. “I’m not citing either of you.” She paused, expression daring either of them to react. “Even though I absolutely could and _would_ if I thought it would do any good. And I’m not grounding Cas, since that barely even counts as punishment for him.” Cas stared down at the floor, feigning interest in the swirling patterns on the rug. “As for you, consider yourself grounded permanently _._ I don’t give a rat’s ass how Tom, Dick, or Harry’s parents make the rules, but I raised you both better than this.” 

Jody paused, collecting her thoughts.

“You’re _kids_ for Chrissakes, and I don’t mean that in a patronizing way. It’s _literally_ my job to uphold the law and to raise you right, which in this case means no underage drinking with a bunch of hooligans,” she looked pointedly to Jess. “ _Including_ parties where other people are drinking even if you don’t. The law won’t distinguish and neither will I. No parties and no more sneaking out to concerts until you’ve both gone to one of the department’s alcohol awareness seminars and done some extra chores around here.”

Cas’ eyebrows shot up. How did Jody know about _Homo-A-Go-Go_?

Jody sighed. “You’re not as sneaky as you think. Now both of you, get yourselves to bed. You’re in for one hell of a morning.”

Cas trudged up to his bedroom, his thoughts racing. Jess spared him a concerned look at the top of the stairs and Cas ignored her, slamming the door closed.

He felt so stupid, letting Brady get under his skin again, and the utter mortification he subjected himself to in front of Dean. And now, to top it all off, Jody was beyond disappointed in him, ruining any chances he had of convincing her to endorse his pursuit of studies back East. He was better than this. He flopped onto the bed, rolling onto his side with a groan. He’d just go back to focusing on getting out of high school in one piece, avoiding romantic entanglements, and getting his life on track. 

He had a foster mom to prove and a point to make proud - or maybe it was the other way around. He would figure it out in the morning.

~~~~~~~~

Dean shrugged off the canvas jacket he’d had to take this morning, feeling exposed without his usual leather one as he walked into Henricksen’s first period class on Monday morning.

Students lined up at his desk, plopping down completed essays and returning to their seats, faces as grave as if they were signing their own executions. Dean liked the English teacher well enough, but Dean made a point of avoiding the class nonetheless, especially after Vonnegut had been cut from the syllabus by class vote. 

“All right, not that I care, but how was everybody’s weekend?” Henricksen attempted to get the attention of the class.

Brady drawled, “Oh, I don’t know. Maybe we should ask Castiel.” 

“Unless he kicked the crap out of your dumb butt, I don’t wanna hear about it.” Henricksen swiftly changed the subject. “Okay, let’s open up our books to page seventy-three, sonnet one-forty-one. And listen up.” 

Dean zoned out as Henricksen cleared his voice and recited the sonnet. He spent that time looking over at Cas who refused to meet his gaze. In fact, Cas was the most attentive person there, book opened to the sonnet and hand poised to take notes. Dean tuned back in just in time to hear Henricksen’s newest assignment. 

“Now, I know Shakespeare’s a dead white guy. But nevertheless he knows his shit, so we can overlook that. I want you all to write your own version of this sonnet.”

Cas raised his hand.

“Yes, Mister I-have-an-opinion-about-everything?” Henricksen was clearly not in the mood for Cas’ usual commentary. 

“Do you want this in iambic pentameter?”

“You’re not going to fight me on this?”

“No. I think it’s a really good assignment.”

The teacher narrowed his eyes, back tense. “You’re just messin’ with me, aren’t you?” Some of the students tittered and Dean watched the teacher’s rising temper with a mixture of interest and dread. 

“No. I’m really looking forward to writing it,” Cas said earnestly. 

Henricksen snorted. “Get out of my class.”

“What?” 

He thrust his arm towards the door, nostrils flaring. “Out. Get out!”

“Thanks Mr. Henricksen,” Brady snickered. 

“Shut _up_!”

Dean watched Cas leave, still steadily ignoring Dean’s presence, and made plans to find Sammy and Charlie after class. As much as he wanted to run after him he knew it would likely only result in Dean getting the crap kicked out of his own ‘dumb butt’. For the time being, he opened his notebook and began going over Henry’s finances again. 

~~~~~~~~

Charlie hovered in the hallway by Gilda’s locker. She could totally do this, it was just a recon mission. For Sam. For The Plan. She took a deep breath and was about to walk over when a sweet voice called out. 

“Charlie?”

“Right in one.” She aimed for nonchalant and asked, “What’s up?”

“The usual BS.” Gilda hefted the textbooks in her arms for emphasis. Her eyes flicked over Charlie and her tone brightened. “You look well. Hangover not too bad?”

“Not at all. Truth be told, I’m not much of a drinker.”

“That’s probably for the best. You don’t exactly look like a heavyweight.”

Charlie laughed, ignoring how sweaty her palms were getting. Remembering her mission, she flicked her eyes into Gilda’s locker, landing on a photo tacked up on the interior. “Oh! You like Tara and Willow too? I’m really enjoying their friendship.”

Gilda looked at Charlie sidelong, and repeated slowly, “Yeah . . . friendship.” Her eyes were twinkling. Her tone brightened and she said, “I suppose you watch Buffy too?”

Charlie rolled her eyes. “Well, obviously. Being a slayer is pretty much my number one dream in life. The Scooby gang could use someone that actually bothers to carry a wooden stake every now and then, you know?”

Gilda’s smile grew into a grin. “I know exactly how you feel. Sometimes I feel like _this_ school sits right on top of the Hellmouth.”

The girls shared a laugh.

“Listen, I shouldn’t be talking to you about this, but . . .” Gilda bit her lip, considering. “I know why you’re here.”

“You do?”

Gilda’s eyes narrowed. “I’ve seen you hanging around with those Winchesters. You want to know how angry Cas is at that guy.” 

Charlie relented, nodding.

“I love the guy to pieces, but Cas is pretty much permanently pissed off about something. So when I tell you he hates Dean Winchester with the fire of a thousand suns, you should know it’s no joke.”

Charlie grimaced. “That bad, huh?”

Gilda strummed her fingers on the locker. “I’m on Cas’ side here, but even I have to admit he might have overreacted a bit.” 

Charlie asked, “What exactly went down between them after the party?”

Gilda sighed. “Let me put it this way. How would _you_ feel after drunkenly coming onto someone and being rejected? Now multiply that by like, a thousand since this is a dude we’re talking about. Rejection is anathema to them.”

“Yeesh. But I’ll see what I can do.” Charlie nodded abstractly, the gears of a forming plan already turning.

Gilda smiled, placing a hand on Charlie’s shoulder and squeezing. “Good luck. Regardless of how it turns out, I hope to see you around, Slayer.” 

~~~~~~~~

Dean took a break from eating his slimy salad to watch in fascinated horror as Ash stuffed an entire slice of pepperoni pizza into his mouth. Despite his revulsion, his traitorous meat-loving stomach grumbled in protest and Dean dropped his fork and crossed his arms with disgust. He was about five seconds away from grabbing himself a slice, judgmental glares from you-know-who sitting alone at his own table without any food be damned. What point was there in pretending to be vegan to get this guy to like him when he clearly relished hating him?

Right before standing to his feet, Dean was cut off by Sam plopped down next to him with his tray. Ash stopped chewing mid-bite, shooting Dean a meaningful look and rose to his feet, mumbling something like, ‘Catch up with you later, man’ around all that food.

Dean went back to sneaking glances at Cas, merely grunting in acknowledgement of his brother. Sam followed Dean’s line of sight and exhaled, expression troubled. 

“What’d you do to him?”

Dean looked down at his hands, not making eye contact. “Nothing. Dude was drunk, I drove him home.”

“I thought he was finally starting to like you.”

Yeah, until Dean put the kibosh on . . . whatever they had been doing in his car. “How’s it going with Jess?” Dean hoped Sam wouldn’t give him a hard time for the abrupt subject change.

Instead, Sam’s eyes lit up. “Well, I drove her home too, not long after you left, and we got to talking. We’re . . . gonna take it slow.” 

Dean rubbed the back of his neck. “And uh, this chick, she’s . . .”

“No, she’s not another drug addict Dean,” Sam scoffed.

Dean exhaled with relief. Sure Sam passed through rehab with flying colors, but it didn’t stop him from worrying. He was saved from having to say anything else when Charlie sidled up next to them, buzzing with energy.

“Hey guys. Alright, I got the lowdown from his friend Gilda,” she announced, slightly out of breath.

Sam perked up. “What did she say?”

“Well, apparently Cas ‘hates him with the fire of a thousand suns’.” She looked pointedly towards Dean. “And that's a direct quote.”

“Thanks. That’s very comforting of you.” Dean faked a smile, flicking his flimsy plastic fork across the table. It felt like every baby-step forward with Cas was always followed by a stumble backwards.

“We don’t know. He could just need a day to cool off,” Sam suggested, trying to be Mr. Optimism. Sam looked back across the lunchroom, catching the nasty scowl that Cas directed towards Dean.

“Maybe two.” Sam amended, grimacing. 

Dean frowned, skeptical. If Cas resolved to hate Dean’s guts, what could he possibly do about it?

Charlie looked between the Winchesters and their twin morose expressions. She rolled her eyes, then spoke like she was talking to a pair of first graders. “Look, you guys, it’s a simple solution. Sure, the guy’s pissed, not because you did something _wrong_ per se, but because you embarrassed him.” She pointed at Dean. “Sacrifice your dignity and even the score.”

Dean scowled but her words catalyzed a forming idea in his head. He patted Sam on the back and called back to Charlie, “Thanks Miss Frizzle,” before leaving. He had to find some _more_ geeks who owed him a favor.

~~~~~~~~

Intercepting Dean, Brady checked both directions down the hallway and then thrust two one-hundred dollar bills at him.

“Here. This should take care of everything. I mean, you’re both dudes, right? Low maintenance? Just make sure he gets to the prom.”

Dean set his jaw. He couldn’t keep doing this to Cas. He had already so much as told Dean there was bad blood between him and Brady, and regardless of Dean’s intentions he knew it wouldn’t end well if it ever got out that Brady was the reason he had started doing this. 

“You know what?” He shoved the money back at Brady. “Get lost. I’m sick of playing your little game.” 

Brady’s eyes blazed, but he restrained himself enough to ask, voice tight, “You sick of, let’s say, three hundred?”

Shit. Three hundred in addition to what Brady had already given him for the other dates was a lot in his household. He thought about Henry and hesitated. This money combined with the savings from his job at the car wash would essentially put them in the clear. 

Dean felt pained, but took the money back from Brady, crunching it in his fist in his jacket pocket. 

“Fan-frigging-tastic,” he muttered to himself as he made his way towards the shop room.

~~~~~~~~

Jess was focused on shading her sketch when she heard footsteps behind her. 

“You're concentrating awfully hard considering it's _art_ class,” Brady commented, leaning on his elbows. 

“Can I help you?” Jess tried her best to sound polite, but wasn’t sure she completely hid her annoyance. 

Brady bumped her arm, grinning. “I want to talk to you about prom.” 

Jess sucked in a breath as his movement caused her to press too hard into the paper. If she was being honest, and she’d never admit it to their faces, Jody and Cas were right. Brady was a self-absorbed douche who wasn’t worth half the trouble, and she had no desire to go to next period with him much less _prom_. It was hard to completely let go of her desire of fitting in and keeping up with the rest of her friend group.

If anything, she had been thinking about what it might be like to go with Sam. Their friendship was barely off to its fresh start, but he seemed like a genuinely good person. A little misguided and nervous, but good. 

Luckily, she could try and use her one out now. “Look, you know the deal. I can't go if Cas doesn't go.”

Brady sounded smug. “That won’t be a problem.”

Jess looked back to her sketch. “Oh? And why is that?” 

“Let’s just say a little birdy told me that your brother is going.”

Jess balked. “Since when?”

Brady was quiet just a moment too long for her liking. “Don’t act so surprised. Even the freaks still go to prom.”

He sauntered away and she shook her head in frustration, pushing the conversation to the back of her mind as she went to fetch paint.

~~~~~~~~

Cas walked with Gilda outside after classes, enjoying the emerging sunshine. He spotted another prom flyer and tore it down without pausing in his chatting with Gilda. 

A girl a few feet away groaned. “Not _again_!”

Cas ignored her, offering the torn poster to Gilda. “Can you imagine who would go to this antiquated mating ritual?”

“I would. But I don’t have a date.” Gilda said dreamily, cradling the poster. 

Cas narrowed his eyes, looking sidelong at her. “You really want to get all dressed up just so some over-cologned jerk on the dancefloor who’s too drunk to remember you’re one of the school’s flaming homosexuals can grope your ass? All while in a room full of more idiots dancing to terrible music?”

Gilda sighed. “Assholes groping me are an occupational hazard regardless of whether I go to the dance or not; I’m perfectly capable of defending myself. But fine.” She threw out her hands. “We won't go. It's not like I’ve got a dress anyway.”

“You’re looking at this from the wrong perspective.” Cas tried to point out. “We're making a statement.”

“Oh, goody! Something new and different for us.” Gilda didn’t try to hide her sarcasm. 

Cas balked at her tone. Since when was his best friend so gung-ho about being prom queen? A bunch of drunk teenagers did not make for a good time; he’d re-learned that lesson the other night. It was stupid to spend so much time and energy for a night of crappy music, even if you somehow landed a halfway-decent date. How could people like them ever enjoy the corny theme decorations, the judgmental chaperones, the corsages and the punch and embarrassing dance moves? Castiel imagined green eyes sparkling as they danced close under dimmed lights . . .

He snapped out of it as he found his thoughts drifting to Dean _again._ He bid farewell to Gilda with a hug as she turned to head home. He was going to be late to practice if he didn’t get a move on; he’d have to deal with his Dean problem at a later time.

~~~~~~~~

Castiel was in the middle of soccer practice when it happened. The team was congregated in the middle of the field, drinking water and listening to the coach describe their next drill. There was a screech and then a smooth voice came over the loudspeaker system. 

_You are my fire_

_The one desire_

_Believe when I say_

_I want it that way_

The team turned to look, raising their hands to their foreheads to shade their eyes and scan back and forth. Cas spotted Dean at the top of the bleachers holding a microphone. It was too difficult to discern his expression, but he was looking right at Cas. 

Holy shit. 

“Holy shit,” one of his teammates said. “Is this another promposal?”

_But we are two worlds apart_

_Can’t reach to your heart_

_When you say_

_That I want it that way_

Dean was singing to him _a cappella_ in front of everyone. He blushed. How did Dean know this song was his guilty pleasure? Dean motioned to someone and before he knew it, the marching band was storming the field, the loud brass instruments a little unpracticed yet making up for it with jubilance and deafening sound as Dean continued his serenade.

_Tell me why_

_Ain’t nothing but a heartache_

_Tell me why_

_Ain’t nothing but a mistake_

_Tell me why_

_I never want to hear you say_

_I want it that way_

As he continued the song, Dean started dancing around the bleachers and Cas couldn’t hold back his smile, clapping his hands to his mouth. This was the greatest thing he’d ever seen. Dean had a fairly nice singing voice, but the dorky dancing was what truly made the routine golden. 

Dean got cornered by two security guards, but managed to dance out of their hold and run away. The entire soccer team, including Cas, applauded him, even as the coach yelled at them to get back to practice. 

After leaving the locker room, Cas walked to the parking lot slowly, distracted from his sore, depleted muscles by the image of Dean shaking his hips and fleeing from the fat security guards still occupying his mind. Plus the fact he had gotten the school marching band in on it, somehow, and performed the whole act in front of everyone in the stadium? It was absolutely surreal. 

He found himself wanting to _thank_ Dean for the diversion, even though he was supposed to still be hurt and angry and moving on from that night of his lapse in judgment. Instead, his resolve didn’t feel so right anymore; the anger wasn’t there to back it up. Somehow, without his conscious permission, he’d already forgiven Dean, and himself. Staying mad was . . . pointless. Impossible.

Feeling emboldened, Cas decided to find Dean. He frowned, thinking. Despite how often Dean had been popping up in his everyday life recently, he still barely knew the guy. He didn’t even know where to look.

He made his way to the parking lot, brainstorming what he could do. Maybe he’d corner Dean after English, if he bothered to even show up. Cas huffed as he recalled how rarely Dean deigned to show up to class, usually only bothering to show his face when an assignment was due. 

He arrived at his car, noticing an older black car parked next to his in the relatively empty lot. He got in his Continental without thinking much of it. As he went through the motions of turning the keys and setting up the tape deck, he caught a glimpse of someone unlocking the car next to him. 

He snorted. What were the odds that he’d park right next to Dean today? He rolled down the passenger-side window. 

“Hey Nick Carter, great show today,” he called out. 

Dean turned around, smirking when he spotted Cas inside the car. He sauntered up towards the open window and leaned down, crossing his arms on Cas’ door and grinning at him through the open window. 

“I hoped you might like that,” Dean said. 

“So tell me how’d you manage to outrun the security guards?” Cas asked, smirking. “Your stamina’s improved since the last time I saw you on those bleachers.”

“Well whenever handcuffs are involved . . .” Dean trailed off, waggling his eyebrows. 

Cas rolled his eyes, blushing. A thought occurred to him and he twisted around, rummaging in the back seat before pulling out Dean’s leather jacket. Without a word he folded it into quarters and held it out through the window. 

Dean brightened. “Thanks, Cas. I know I said I would let you keep it, but that was more of an expression tha—”

Castiel shook his head and demurred, “It suits you much more.”

After a pause, Dean spoke again, his tone contrite. “About the other night.” He rubbed the back of his neck.

Cas shook his head again. “You really don’t need to—”

“I really do. You know what they say about relationships and communication.”

Cas tilted his head. “I don’t think I do.”

Dean barked out a laugh. “Yeah, okay, me neither.” Sobering, he continued, “I just wanna make it crystal clear that it wasn’t for lack of consent on _my_ part. I just don’t go there with people after they’ve been drinking.”

“I reasoned it was something like that after I sobered up and my mom read me the riot act.” Cas tested, “How do you feel about round two? Minus the blackout drunk date, that is.”

“I thought you’d never ask,” Dean smiled. “Pick you up at six?”

“Isn’t it _my_ turn to drive?” 

“No way! My date, my car.”

“Then it’s your dime too, Winchester.” Cas rolled up the window and pulled out of the spot, smiling the whole way home. 

~~~~~~~~

Dean did his best to ignore his nerves as he drove. It was far from easy; after so many false-starts with this guy he couldn’t afford to screw up, and screwing up was the one thing Dean knew he could rely on accomplishing. He remembered Sam’s words from what felt like ages ago: _“The counselor taught me a trick for anxiety, Dean. Rather than try and calm down, channel your nerves and say ‘I am excited!’ Your brain will turn the negative into a positive.”_ Dean didn’t buy into most of the New Age-y crap from Sam’s rehab but the words stuck with him. _I am excited._

He looked over and smiled to himself. It would be dangerously easy to crash, sneaking so many glances at the attractive passenger in his car. He looked good, if a little stiff. Maybe the guy was nervous, too.

They spoke very little in the car, mostly small talk about school. Dean was too nervous to steer the conversation to Cas’ family, since both he and Sam had implied relations with his sister were less than friendly. He avoided music bands too, since he wasn’t confident enough in his knowledge of the queer punk scene. Luckily the only exclusively-vegan place around wasn’t far and he parked in a spot close to their destination, backing in with practiced albeit slightly exaggerated ease. He hurried out of the car to reach Cas’ door and hold it open with a dramatic flourish. 

“So, uh, I figured we could grab some dinner and then walk around a bit,” Dean smiled as he led the way towards their destination. “Get to know each other a little, ya know? Forecast promises it’s gonna be clear all evening.”

They walked side by side past a few storefronts before Dean stopped, pulling his hand from his pocket and checking the smudged writing for the address. The restaurant, called _The Veggie Table_ , looked inconspicuous enough, if a bit dim. He shrugged at Cas and followed him in after propping the door open. 

Horrendous pepto-bismol pink carpet lined the entire space of the restaurant, and several groups of people were seated in various circles on the floor. Dean wrinkled his nose. It looked like it was run by a cult, if he was being honest. He was starting to wish he’d opted for the Indian place instead, even though curry gave him terrible gas. Cas gave Dean a long look, expression inscrutable.

A short bearded man dressed in a flowy white tunic and linen pants approached them and greeted, “Good evening, and welcome to _The Veggie Table_. We’re a little full right now but can seat you in about ten minutes.” Inexplicably, the man bowed before retreating back into the kitchen.

Dean’s eyes flicked back to the door to the street, then back to the circles of colorfully dressed customers. The place screamed Jonestown to him in a big way, but if this was vegan dining he’d have to man up and suffer his way through. He’d just be sure to avoid any Kool-Aid. 

“Ah, Dean,” Cas cleared his throat. “Where are we exactly?”

Alarm bells rang out in Dean’s head, panic mounting at Cas’ bewildered expression. Crap. Was this not the right kind of place? He didn’t know much about hippie places. 

He scrambled to form words. “Well, I uh, I figured you’d like a vegan place, since you’re—” He gulped and scratched the back of his head, stopping abruptly when he recognized it for the nervous tic it was. “You know, a vegan and all about saving the bees. So I just thought that—”

Cas bit his lip, trying to hide a smile. “As cute that I find it that you were trying to impress me by going out of your comfort zone, I’m not,” Cas chuckled. “A vegan, that is. I tried about a year ago, but I have to admit I just couldn’t give up cheeseburgers.” 

Dean’s eyes bulged and he gaped in shock. “You mean, you don’t—” He gulped. He was going to murder his brother and that friend of his.

Cas peered outside. “You want to get out of here before someone comes over and tells us about their ‘special corner on a higher truth’? I think there’s a Dick’s a few blocks down that way.” 

“Definitely.” Dean nodded and held the door open. 

At first, the short walk to Dick’s was silent and awkward. Dean tried hard to not show his embarrassment at his initial choice of restaurant. 

Very suddenly, Cas came to a stop and burst out laughing, clutching at his sides. 

Dean watched him with a startled expression, and Cas explained between deep breaths, “I’m just so confused! Why is it called _The Veggie Table?_ There were no tables! Everyone was sitting on pillows eating off of the ground.”

Dean cracked a grin and said, “Oh thank God,” he exhaled, dropping his head in relief. “I’m glad it wasn’t just me. Full-on Heaven’s Gate back in there.” 

~~~~~~~~

They stood in the line at Dick’s and each ordered cheeseburgers and shakes, strawberry for Dean and chocolate for Cas. Dean handed the cashier his payment with a closed smile and the two boys huddled off to the side to wait for their food.

When their order was up, Dean grabbed their bags and handed one to Cas.

Dean watched as Cas greedily unwrapped his burger and bit into it with a moan, smirking as he noticed Dean’s eyebrows shoot up.

“I take my burgers very seriously, Dean.” His matching expression gave way to a smile. “These make me very happy.” 

Dean slurped at his milkshake. “That’s how I feel about pie.” 

They fell back into silence while they ate, slowly meandering in the waning light.

“You know, even if I _were_ vegan you wouldn’t have to be too. It’s a personal lifestyle choice anyone is free to make, or not to make. Pretending to be something you’re not is just foolish and sad.”

“That so? Does this mean I can take up my ‘lifestyle choice’ of smoking again?”

Cas scowled. “Don’t even _pretend_ like those are analogous. Do you realize how much dama—”

“Easy, Cas. It’s a joke.” He looked at Cas head on, a smile breaking across his face. “Here, you’ve got,” He reached his hand out to Cas’ cheek, wiping away a spot of ketchup at the corner of his lip. 

Cas shivered, and Dean looked down at their milkshakes. “It’s a bit chilly after these, isn’t it?” Cas nodded dazedly and Dean took their empty containers and wrappers, tossing them into a trash bin. He rubbed his hands together, blowing his hot breath into his palms.

They followed the path into the Pacific Science Center, taking a seat on one of the benches. Shivering again, Dean scooted close, reaching for Cas’ hand. He pressed it between his palms and clarified gruffly, “You know, for warmth.”

Cas smiled slyly, interlacing their fingers without a word. He was looking at Dean and Dean found it oddly easy to go on staring back. The silence should have been awkward, but wasn’t. He was sure they looked like a couple from some Meg Ryan movie and anyone walking along the path was probably gagging. Usually _he_ was the guy gagging, but now that he found himself in the position of those PDA-happy assholes? He couldn’t care less.

The arches began to light up colorfully and both Dean and Cas stirred from their reverie at the descending darkness. 

Dean cleared his throat, a question occurring to him. “So what’s your excuse?”

“For what?”

“You know, acting the way we do.”

“I don’t like to do what others expect,” Cas shrugged. “Why should I live up to someone else’s expectations?”

“So you disappoint them from the start and you’re covered, right?” Dean retorted. 

Cas chewed his lip. “Something like that.”

Dean squeezed his hand lightly. “Then you screwed up.”

“How?” Cas’ eyes bordered on accusatory.

“You never disappointed me.”

Cas’ furrowed expression gave way to a shy smile. 

“So, can I ask what the deal is with your family? Your sister and the Sheriff, right?” Dean asked, clearly nervous to be broaching the topic. 

“I’m surprised you haven’t heard by now.” 

Dean shrugged. “I’m not real big on high school gossip.”

“Well, Jody took in Jess after she lost her family. As for me,” Cas exhaled. “You remember the Branch Davidians?”

Dean creased his brow. “You mean the cult in Texas? With the siege and that shoot out?”

Cas nodded. “People don’t realize something like that happened here in Washington too, on a smaller scale. I don’t remember a lot, apart from—”

Dean held out a hand to stop him. “Whoa, hang on, you’re not joking?” 

“Is it...funny?”

“No, no.” Dean rubbed at his forehead. “Sorry, go on.”

“Well, a few years before Waco, Jody was working out by Spokane investigating the Naomites for weapons violations. Like I said, I don’t remember much of life there, but apparently they were endangering us children with the living conditions there. Afterwards, when she got me out, Jody and I connected. Neither of us wanted to put me in the system, so she took me in and I’ve been with her ever since.”

“Wow, that’s…” At a loss, Dean blinked. “You must love her a lot.”

“Mhmm,” Cas hummed back. He squeezed Dean’s hand, then relaxed his posture and said in a lighter tone, “We have a Sheltie at home.”

Dean looked up at the sharp turn in topic.

Cas elaborated, “Jess named him Leo, since she was obsessed after seeing Romeo and Juliet in theaters. I made a fuss about it at the time, but even I can’t deny he’s extremely attractive.” 

Dean threw his head back and laughed. “Anyone who says he isn’t hot is just lying.”

“Now you go,” Cas said.

“Jeez Cas, it’s hard to follow something big like that.” At Cas’ uncertain expression, Dean added, “I mean, we don’t even have a _fish_ much less a fancy dog.” Cas rolled his eyes but smiled. Satisfied, Dean shared more, tapping his shoe against the pavement while he spoke. “My brother and I live with our grandfather. Took my sorry ass in after my dad kicked the bucket, but I’ve always looked up to him since I was a kid. Gramps was a World War II Vet turned college professor, and he always told the best stories. I used to want to be just like him when I grew up.” 

“He means a lot to you,” Cas offered earnestly. 

Dean shrugged. “My dad was never the greatest, but he was always there for me. Not a lot of people were.”

There was a brief silence as Dean’s words sunk in. Cas squeezed his hand again. They watched more pedestrians pass by, the stream of people thinning out more and more. 

“You up for it?” Cas inclined his head toward the Space Needle. 

“I’ve actually never been,” Dean admitted, glad for the change in subject. 

“Then we have to go,” Cas said, determined.

They made the short walk to the ticket booth and Cas pushed Dean aside to pay the entry for both of them. Dean scowled but reached out for Cas’ hand again as they made their way to the elevators. The operator ushered their group onto the elevator and it smoothly glided up to the top. Cas pulled Dean to the door to the outdoor observation deck.

Dean shook his head slowly. “C’mon, Cas. I can see fine from here. No one else is going outside.”

Cas tugged, insistent. “You have to feel the rush of the wind, trust me.”

Dean eyed the platform a little uneasily, but let himself be led outside. It was much colder and windier, and Dean pulled Cas in close for warmth and comfort. Cas held onto the railing and breathed in long and deep, a content smile breaking across his face. They both scanned the water, shining with the last dregs of sunlight mingled with the awakening lights of the city. Everything twinkled and shone from so high above but the air was silent except for the whistling gusts of wind. Dean’s stomach flipped uneasily in protest of the altitude and he looked away from the dizzying panorama back to his date. 

“It’s beautiful up here,” Cas said, looking more serene than he’d ever seen him as his hair fluttered in the breeze.

Dean studied Cas’ profile and drawled, “Yeah, it really is.”

Cas shook his head at the line but couldn’t help but crack a smile. He looked back out over the skyline. When he trembled again, Dean drew closer, resting his chin on Cas’ shoulder and wrapping his arms around his chest. “This okay?” he whispered against his ear, red from the brisk air.

Cas nodded, his breath catching for a second before evening out. They stood still together, comfortable in each other’s warmth and silence. After a time, a loud-speaker announced that the observation deck would be closing in ten minutes, so they slowly extricated from each other and made their way back to the elevators and rode back down to Earth. 

They walked back through the path under the arches, cheeks red and smiling. Cas turned to Dean and asked, “What did you think? Worth the hype, right?” Dean shrugged. Cas tossed his head. “Oh, come on.”

Dean capitulated, “I liked it! The view was fantastic, don’t get me wrong. It’s just a bit...windy.”

Cas knocked against his shoulder. “ _Someone_ must be afraid of heights.”

Dean scoffed, “Am _not_ ,” and bumped Cas back.

With a gasp, Cas stumbled at the contact, arms windmilling as he struggled to catch his footing. Before Dean could even turn, much less reach out to grab him, Cas was landing in the pool of water in the fountain with a loud splash. 

“Cas!” Dean yelled, kneeling at the edge and squinting his eyes in the dim light, searching for the other boy in the dark water. “Son of a bitch.”

Cas rose to his hands and knees spluttering, spitting water out of his mouth and coughing. Dean hopped down into the water and hissed at the cold, glad that it only came up to his knees. He walked Cas back to the ledge and helped him up. When they both clambered back on solid ground, breathing hard, Dean looked over Cas for any sign of physical injury.

“Are y–” Dean clutched at his side, unable to withhold his bursting laughter. “Are–” His head dropped and he shook with mirth mixed with cold, then tried again. “Are you okay? I mean physically?”

Cas looked over at him from his spot on the ground, teeth chattering and water still dripping in streams from his nose and ears onto the pavement. In the darkness, he looked like a cheaper version of the creature from the black lagoon. He wore his signature glare, albeit a less steady one as he trembled. “I’m. F-f-fucking. _Cold_.”

Dean only burst out laughing again, trying unsuccessfully to lift himself to his feet. Eventually he managed to get upright and yanked Cas by the shoulder up as well. “C’mon, let’s get out of here. I think I have some towels in Baby from when I went out to Lake Union a few weeks ago.”

“B-baby? You c-call that. Mon st-ster of a car _Baby_?”

Dean pointed a finger. “You better watch your mouth, or you’re gonna be walking home like that, you drowned rat.” He frowned, then gestured to Cas to remove his coat. Thinking to himself that this was becoming a tradition of theirs, Dean slipped out of his own leather jacket and wrapped it around Cas’ shoulders, hurrying them both back to the car. 

Dean found two towels in Baby’s trunk, flinging one to Cas while peeling off his own water-logged shoes. Cas dried himself off as best as he could, and Dean rummaged a little further, pulling out a worn AC/DC shirt. 

“Here,” he offered. “Should at least be better than the wet stuff you’ve got.”

Cas took the shirt and hesitated, so Dean averted his eyes back to his socks while Cas changed. 

“Much better,” Cas said, and Dean looked up to meet his smile. “Thank you.” His voice was rough but otherwise back to normal, so Dean figured he would be okay. 

~~~~~~~

“We’re quite the pair aren’t we,” Cas commented once they were rounding the corner onto the street for the Sheriff’s house. “The angry, gay foster kid and the mysterious loner orphan who sold his liver on the black market.”

Dean laughed. “None of that stuff is true.”

“What, no jail time?”

“Not _yet_. Uh, dead guy in the parking lot?”

“Rumor. How about the grave desecration?” Cas hedged.

“Hearsay.” Dean drummed against the steering wheel. “Ooh, I got one. Raphael’s balls?” He raised an expectant brow.

Cas smirked. “Fact. But he deserved it. He tried to grope me in the lunch line.”

“Fair enough,” Dean shrugged, frowning. He put the car in park once they reached the house, but Cas didn’t seem to notice. 

“Where were you last year? I know the porn career's a lie.”

“Do you?” Dean waggled his eyebrows. 

Cas did not look amused. “Tell me something else true.”

“For the record, I’m _not_ afraid of heights. But I do hate flying.”

“No!” Cas protested, punching Dean’s shoulder. “Something real. Something no one else knows.”

“Okay. I think you're sweet.” Dean smiles coyly. “And a bit of a weirdo who drives a biofuel pimp car. And cranky. But sexy. And _completely_ hot for me.”

Cas scoffed. “You're amazingly self-assured. Has anyone ever told you that?”

“I tell myself that every day, actually. I think I’m adorable.” Dean grinned, teasing at Cas’ wet hair. The guy looked smaller than he was, wearing just a T-shirt and wrapped in a towel. He was so used to Cas’ cornered alley-cat posture, this vulnerable Cas caught him off guard, reminding him more of that night of the party. He blurted out, “Go to the prom with me.”

Cas rolled his eyes. “Ha ha. Good one.” 

More earnestly, Dean leaned closer and said, “Nah, for real. Let’s go together. We’re both seniors, it’s our last chance.”

“No.” Cas drew the towel tighter across his shoulders. 

“No? You already have a date?”

“Don’t be an idiot, Dean.”

Dean pressed, “Why not?”

Cas was firm. “Because I don't want to. It's a stupid tradition.”

“Well, yeah. I know that. But that’s why people won't _expect_ you to go.” Cas’ mouth twitched at that, and Dean felt a small triumph. He recognized a fish on the line. “We’ll do the whole thing Cas-style, with the suits, the limos, the dancing. We’re not the suckers if we’re doing it all ironically, right?” Realizing the engine was still rumbling, Dean removed the key from the ignition and looked to Cas with as reassuring of an expression as he could muster. “I’ll tell you what, I’ll even do a reprise on stage, dancing and all.”

Cas relented, a smile tugging at his mouth. “Offering to make a fool of yourself, again? At a fancy venue? You know all my weaknesses, Winchester.”

“Well, not _all_ of them. Not yet.” Dean leaned in to meet Cas’ lips, hesitating a hair’s breadth away.

Cas kissed back eagerly and Dean’s hands immediately roamed over Cas’ body, easing under the borrowed shirt, spurred on by Cas’ breathy sighs. 

“Like seeing you in my clothes,” Dean murmured as he crowded closer to Cas. “So hot.”

Cas’ breath caught and Dean felt a thrill shoot up his spine at the sound. He pressed a palm against the other boy’s heart, feeling the pumping rush of blood as they both squirmed and shifted for closer, warmer contact. So lost in the kissing, Dean belatedly noticed the Impala’s windows fogging up and he pulled away, his lips parted and swollen. Both of them were practically gasping for breath. 

In a breathy whisper, Dean asked, “Does that count as a yes?”

The porch lights from the house flickered on, and Cas flicked his gaze to them. “Shit, I should probably be getting in soon.” Cas drew away and pulled Dean’s borrowed shirt back on. “Thanks for a lovely evening, Dean.” After leaning back in for one last quick kiss, he added, “That’s a yes.”

Dean let out a breath he didn’t know he’d been holding. He was in so far over his head.

~~~~~~~

The following day, Charlie was packing up her bag after her last period when she noticed Gilda making her way towards her locker.

“Hey Charlie,” she greeted, a little out of breath. “I’m glad I caught you before heading out.” 

Charlie nodded dumbly.

Gilda confessed in a soft tone, “I haven’t been able to stop thinking about you since the party.” 

Charlie blushed. “I—me too.” She internally shook her head. There was just something about Gilda, that she couldn’t think straight whenever she was around. Oh.

Well now, there was a thought.

She _wasn’t_ thinking _straight._ It definitely explained a lot of feelings she’d been ignoring recently amidst all the drama of being thrown out of her friend group and keeping up with school and extracurriculars. 

“So what do you think? I know it’s _super_ last minute.” Gilda prompted. 

Charlie shook herself out of her thoughts. “Uh . . . what was that? Sorry I zoned out for a sec there,” Charlie blushed.

Gilda smiled, undeterred. “I was wondering if you’d want to go to prom with me? By some miracle, Cas has suddenly decided to go, so the protest is off. I have a beautiful dress and now all I need is a beautiful girl to accompany me.”

“I’d love to,” Charlie answered a little breathless but without hesitation. It wasn’t until Gilda had sped off that her words sunk in fully and Charlie clapped a hand to her mouth. She had a date. To the prom. With a _girl._

~~~~~~~~

Later that night, Jess timidly entered the living room where Jody was seated, Leo curled up in his usual spot on the couch by her side as she cleaned out her service weapon. 

“Jody?”

“Hey, honey.”

“Um. I wanted to discuss tomorrow night. As I’m sure you know, it’s prom night . . .”

Jody set her supplies down on the table and crossed her arms. “Aren’t you grounded?”

“Well yeah, but—”

“And does Cas have a date?”

“Well, no. At least I don’t think so.”

“Then I’m not sure what you’re getting at. You know the rules in this house. If Cas isn’t going, you’re not going.”

“So let me get this straight. There’s Cas who’s not interested and me, _dying_ to go.”

“Yeah well, ‘dying to go’ has never landed teenage girls in my morgue. Do you know what can happen at proms or after them?”

“Yes, I do as a matter of fact! We’ll dance to ‘Shout’ and drink _un-spiked_ punch and pose for a dorky photo and then come straight home! It’s not exactly a crisis situation.”

“I’m pretty sure you still have a chore list as long as my arm after the last stunt you pulled.”

“I’ve been working on them! They won’t be going anywhere! Why can’t we put all that aside, so that I can have just one night?”

Jody barked out a laugh. “If I had a dollarfor every parole violator that ever said _that—_ ”

“I’m not a criminal, Jody! And I’m not a corpse! I’m a teenage girl asking for a few hours of teenage normalcy, to not miss out on more things since I’ve been in the system. I can’t live the rest of my life in fear and hiding because some creep murdered my parents when I was a kid.”

“What _is_ normal then?”

“Jody, that’s not—”

“Honey, I know you’re just trying to fit in and be like those girls on those TV shows you like, but you don’t have to change who you are and what you value to be _normal_. And you certainly don’t need to get caught up with people like _Brady._ Just be yourself.”

Jess groaned and stormed out of the room and up the stairs. She flopped down onto the bed and flipped on the old TV she had convinced Jody to allow her a few months ago. Real World Seattle was on—the perfect thing to take her mind off of everything. She got about ten minutes into the episode before there was a soft knock at the door. She rolled her eyes. “Come in.”

Cas entered and leaned awkwardly against the dresser. “Listen, I know . . .”

She ignored him, turning up the volume with the remote but Cas crossed the room and turned off the TV. Standing in front of her, he continued. “I know you hate having to sit at home tomorrow because of me.”

She scoffed. “Like you care. Why are you here? Get out of my room, Cas.”

“I _do_ care.” He paused, making no move to leave. “But I also believe in doing things for your own reasons and not for someone else’s. And I really need you to know that—"

Was he serious right now? She cut him off. “Well, I wish I had that luxury. I missed out on so much growing up, and I would give anything for a night of dancing and normal teenage fun. But no, I’m gonna be cooped up in my room like some loser because _someone_ has to make every second of his life a stupid political statement. Newsflash Cas?” She gestured vaguely around the room with her arms. “No one gives a shit.”

Jess expected Cas to finally leave her alone after that, but her brother just tightened his grip on her dresser and refused to meet her eyes. “I get that you’re lashing out at me right now because you’re angry, but will you just hear me out? This has nothing to do with my ‘stupid political statements.’ I’m trying to tell you something important.” Cas seemed to be looking anywhere but at her. “Brady and I. . .have a history. We went out.”

She couldn’t believe it. “Yeah, right.”

Cas’ eyes widened and he nodded. “Yeah. Like half of sophomore year.”

She couldn’t tell if he was being serious or joking or just manufacturing bullshit reasons for her not to go to prom with Brady. She figured she’d wait and see where this was going, since it wasn’t like Cas knew she wasn’t into Brady anymore. Warily, she asked, “Why?”

“Because he was _such a_ _babe_ ,” he said sarcastically. 

“But you hate Brady.” She tried to piece it together.

Cas looked down at his feet. “Well, now I do.” 

“What happened between you two?”

Cas looked back at her face and raised an eyebrow.

That couldn’t mean . . . could it? He and Brady went all the way? She shook her head in disbelief, nose wrinkling. “Oh. Please, please tell me you’re joking.”

Cas heaved a long sigh, settling at the edge of the bed and then spoke in a rush. “Everyone else in our friend group was doing it, so I did it too. When I told him I wanted to stop being his dirty little secret and that I wasn’t ready for the physical stuff anymore he freaked out and got pissed and cheated on me with some girl. So I dumped him.”

Jess was dumbfounded. If it was all true, she couldn’t begin to imagine the pain her brother had faced secretly. At the same time, it hurt that he had never come to her before with any of this. 

“Anyways, after everything, I swore I’d never do something just because everyone else was doing it and that I wouldn’t hide and be ashamed of who I am. I came out to Jody first, and since then I’ve stuck to that promise. Well, I guess with the exception of Roman’s party.” He chuckled. “And while none of those old friends really cared that I was gay, I just wanted to have a voice again, even though people might hate me for how loud it is.”

“How is it possible that I didn’t know any of this?” She couldn’t let go that no one had told her.

“Well, he didn’t want anyone finding out his secret, and even when I eventually tried to set the record straight, no one believed me.” 

“Why didn’t you say anything to _me_?”

Cas shook his head. “I was ashamed? And still sorting through it all. Then, time went on. Life went on and it got harder to say anything. I wanted to put it behind me.” He frowned. “You didn't really seem interested in my change of social groups or my loud opinions.”

Jess balked. Had she really been so resentful of Cas all these years, that she couldn’t even see when he was hurting? There’d always been friction between them, but for the most part they had always gotten along when they were younger.

“So why’d you help Jody hold me hostage?” Unable to process everything he was saying, she redirected back to prom, so angry now that the words were out of her mouth before she realized what she was saying. “It’s not like I’m stupid enough to repeat your mistakes!”

Cas bristled. “I thought I was protecting you!”

“By not letting me experience anything for myself?!”

“Not all experiences are good, Jess! You can’t always trust the people you want to.”

“You think I, of all people, don’t know that?! And even if I didn’t, now I’ll never be able to find out for myself!” She paused. “Oh, and by the way, it’s not even Brady I want to go out with, which you’d know if you bothered to listen to me every now and then!” 

She crossed the room to get the door open and showed Cas out. She slammed the door behind him, then fell back on her bed.

~~~~~~~

Hefting a bag of groceries, Dean kicked the front door behind him as he entered the apartment and crossed over the the kitchen counter to dump his load. As he drew out the vegetables to rinse under the tap there was a commotion down the hall, like someone falling.

Dean ran into Henry’s room, half-expecting to find his grandfather sprawled across the floor. Instead, he saw the source of the noise, a box that had fallen from the closet’s top shelf and spilled its contents across the floor. He found his grandpa up against the shelving in his closet, arms trembling to support a teetering box that was just out of reach.

“Hey!” Dean rushed to his side and eased the box down from the shelf and out of his grandfather’s hands, carefully setting it on the floor. 

Henry waved his arms through the settling dust, coughing. Henry let Dean herd him into his armchair and he sunk down, still wheezing. Before Dean could ask, he raised a hand and panted, “I’m fine, thanks to you. Nice timing.”

Dean did a quick visual sweep, confirming that the man was unharmed. He tamped down his urge to scold him for not using a ladder. Instead, he gestured to the boxes strewn haphazardly across the floor. “What is all this?”

“I got a letter in the mail from your high school,” he replied. “The yearbook committee is sending out for old baby photos to include for all the graduating seniors.”

Dean got on the ground next to the overturned box, carefully straightening the stacks of documents and folders and sliding them back inside. He flipped one over, lips curving into a smile. “So naturally you decided to pull out old bank statements from nineteen seventy-one?”

They grew quiet when the front door thud shut.

A moment later, “Grandpa?”

Dean exhaled and called over his shoulder, “In here.”

Sam poked his head in the doorway and took in the scene. “Whoa! Did the closet explode?”

“Yeah, a blast from Grandpa’s past.”

Sam plopped down on the floor across from Dean and peeked inside a box, face alight with excitement. “I’ve never seen any of this stuff.”

Henry had replaced his glasses and was parsing through sleeves of yellowing photographs, barely sparing a glance at each one.

Dean picked up a black, newer-looking album. He flipped it open and felt his heart seize. The first photo was blurry, but the outlines of a very young John Winchester and Mary Campbell leaning against a shiny black Chevrolet was unmistakable. He turned the page gingerly, as if handling it too roughly would crumble it to dust. The lovely young face of his mother was smiling or laughing in almost every photo, while his father’s mouth was usually closed but his eyes always trained on the woman. The intense devotion he saw there made him ache. Dean’s breath caught at the photo of Mary in a long nightgown alone in a chair, eyes closed and face serene as she rested a palm on her swollen belly. 

Grandpa Henry cleared his throat and said, “Dean, pass that one to me, will you.”

Dean wordlessly handed the book to Sam, who reached out and gave it to Henry. With his shaky hands, Henry skipped to the last third of the album, squinting at the pages through his glasses. He turned another page and a grin spread across his face as he gazed on the two full-page photos before him. Wordlessly he flipped the book around to show Dean two professional-looking photographs of a baby grinning while wearing a Stetson, bandana and chaps. It was unmistakably Dean. 

Henry abruptly lowered the album and warned Sam, “Careful with that, I think those are your Great Uncle Walter’s ashes.”

Dean snorted and Sam recoiled, his face contorting with horrified disgust as he returned the urn. Dean watched as he reached next for a stuffed photo album, careful not to let any of the loose photos peeking out from the sides fall out.

“This is Grandma Millie, isn’t it?”

Henry squinted at the album in Sam’s lap, and Sam stood up, delivering it to him. Dean rose too, settling behind Henry’s shoulders beside Sam. The three of them looked at the pages together, Henry reading aloud the cursive captions beneath the photos. 

“Millie was a total babe,” Dean said, whistling.

“Dean!” Sam protested, shooting him a dirty look. 

Henry merely chuckled. “Prettiest woman I’d ever laid eyes on. I was checking in on your Great Aunt Margaret at the hospital when she had pneumonia. Back when Harold was in D.C.? Soon as I caught a glimpse of that nurse, I made sure to check in on Marge every day after classes. Of course Millie slapped me silly when I finally got the courage to ask her on a date, figuring I was a philanderer neglecting poor, sweet, ol’ Mrs. Winchester, my ailing wife.” 

It wasn’t the first time he had heard it, but Dean still snickered at the story. 

Sam frowned and asked, “But then how did you know? That she was the one?”

Henry pursed his lips, thinking. “It’s one of those things that accumulates over a long time, then catches up to you all at once. Once we’d gotten past the mix-up about Harold’s wife at the hospital, we went together for a while. Back then people would date in big groups. One of those nights we went out to the movies with a big group, stupid movie, but there was only one other person in that whole theater who laughed when I laughed. Your grandmother, of course. 

“In that absurd instant, I just knew. We always managed to laugh at all the wrong spots in life. Didn’t matter if times were good or if they were bad, that woman always managed to laugh.”

Henry removed his glasses, rubbing at his eyes and smiling. 


	3. ACT III

Cas tightened the light blue bow tie once more and patted at his hair, scanning his reflection in the mirror. His muscles had grown from soccer since the last time he’d worn it, but luckily the suit had been slightly too large when he’d found it. His shoes weren’t the most comfortable and no one would mistake him for James Bond, but he could do much worse. Checking his watch, he crept down the stairs, spotting the back of his foster mom’s head on the couch. 

“Bye Jody, I’m going to prom,” he announced evenly.

She chuckled, not lifting her eyes from her book. “Yeah, sure, okay hun.”

He strode quickly to the door, slipping outside and latching the door behind him. Feeling a little out of breath, he slipped his eyes shut for a beat and took a few deep breaths. When he opened them again, he zeroed in on Dean, dressed in a tux, leaning against his black behemoth of a car. When their eyes met, Dean smiled and spread his arms out for Cas’ appraisal. Cas offered him a thumbs up and descended the stairs. 

“So, where’d you get the tux last minute?” Cas asked.

“Uh . . . just something I had lying around.” Dean replied. Like before, he held open the door with an absurd bow. “What about you?”

Cas thought back to when he bought his tux. There had been a formal event at the senior center, and he had promised Mildred that he would escort her for the evening. He’d gone the whole nine yards, buying the tux at a thrift store and a bouquet of flowers for his date. He smiled to himself, remembering how thrilled Mildred had been. They’d swayed along to old Big Band tunes, raided the dessert table, and posed for a cheesy prom-like photo. She had even kept a framed copy in her room afterwards.

“Well, just something I had . . . you know, lying around.” Cas mimicked.

Dean gingerly shut the door behind him and strode around to take his driver’s seat. He stared through the windshield for a long moment, working his jaw indecisively before reaching into his suit pocket and pulling out a small box and handing it over to Cas. 

“I made this for you,” he said, looking down at his lap. “It’s not Pansy Division or anything, but I think they’re still an okay band.”

Cas looked down at what he now realized was a cassette box and popped it open. In Dean’s neat handwriting it said ‘ _Dean’s Top 13 Zepp Trax.’_ Despite it being one of the biggest romcom cliches, Cas couldn’t hold back a grin. 

“No one’s ever given me a mixtape before.” He leaned over and gave Dean a peck on the cheek, then inserted the mixtape into the tape deck. “Let’s get this show on the road.”

Dean pulled away from the curb, _Houses of the Holy_ blasting from the Impala’s speakers. They get caught in some traffic, stopped beside none other than Billie who glared at them. 

“Looks like you found your perfect match,” she huffed at them through the open window.

The traffic picked up and they arrived at the venue shortly after, following the stream of teenagers in gowns and tuxedos. Dean took his hand as they entered the ballroom. “Let’s do this thing.”

~~~~~~~

Brady pulled up to Jess’ house, recalling the last time he’d laid eyes on the place. Closing out his senior year with some top-grade payback at prom hadn’t even been his idea; he’d have to thank that A/V nerd for his greatest gift since his mom had bought him his Alfa Romeo after Brady had caught her with the pool boy. 

It was a win-win; not only would he be getting some hot virgin piece of ass but it was _Novak’s sister._ He smiled at the thought of Castiel’s face seeing them together. When Winchester kicked him to the curb it would all just be icing on the cake. It was too easy.

He knocked on the door, only to come face to face with the Sheriff herself. He cleared his throat and put on his most charming smile. 

“Hi, I’m here to pick up Jess, Mrs.—” Brady froze. Jess and Castiel were both adopted, so he had no clue what her name was. He glanced down at her hands, which cradled a _gun_. He gulped.

Flicking his eyes back to her face, he was met with a glare from the Sheriff before she slammed the door on him.

~~~~~~~

Jess admired the decorations in the ballroom, still in awe that she had somehow managed to make it the prom. She didn’t have the perfect picket fence life, but she’d somehow managed to fit in with the popular kids and make it to here. It felt great, but also empty. She didn’t really have any real friends, and constantly trying to keep up with people who were so different from her was _exhausting_. 

Shortly after Cas had announced his departure, she approached Jody to tell her that she would be joining Cas at the prom and simply waltzed out the door before Jody could recall the grounding. Plus, it was _her_ rule anyways. 

Sam lead her over to the corner of the room where a red-headed girl was standing with Gilda. 

“Hey guys!” he exclaimed, turning towards Jess. “I’m sure you already know Gilda, and this is Charlie, a good friend of mine and also Gilda’s date.” 

“Nice to meet you Charlie,” Jess smiled back.

“You too,” Charlie said, sounding genuine. “You know, I wasn’t sure about this whole thing but after everything’s Sam’s told me you seem pretty cool. I’m sorry for being so judgemental.”

“I get it,” Jess said. “To be fair, when I met Sam I wasn’t acting like my best self.”

Charlie chuckled. “Well, hopefully we’ll be seeing more of you around. Now if you’ll excuse me, this is my favorite song and I want to dance to it with my beautiful date.”

The two girls hurried off onto the dance floor, leaving Jess with Sam. They made pleasant small talk, before heading over to the dance floor.

They swayed awkwardly, but it was still the most fun she’d had in awhile. She excused herself to the bathroom after a few songs. 

Jess stared intently into the bathroom mirror as she and the other girls inside fixed their hair and straightened out their dress. 

Even Sam Winchester had turned out to be a pleasant surprise. Not only had he held all the doors open for her and made polite, interested conversation, he had turned out to be genuinely _funny._ She smiled just thinking about him. It was about time she rejoined him for another dance. 

As she turned to leave, Rhonda of all people emerged from a stall. 

“What are you doing here?” Jess asked, incredulous. Rhonda was the kind of girl who would rather wear out of season hand-me-downs than be seen without a date at the prom. 

Rhonda sneered. “Surely you realized _some_ of us can manage to land a real date to the prom? Brady just picked me up.” 

Jess internally rolled her eyes. It was laughable that Rhonda would look down her nose at Jess for coming with Sam when _her_ date was a closet-case douchebag. She put on a fake smile. “Congratulations, he’s _all_ yours.”

“Very generous, princess. Oh? And just an FYI, Brady only wanted you for one reason. He had a bet going with the football team about how quickly he could get with the wanna-be foster kid.” Her face contorted into a nasty smirk. “He was going to nail you tonight.”

Jess’ head was reeling. Cas had been right all along. She stormed out of the bathroom and headed straight towards the ballroom. 

~~~~~~~

Never in a million years would Dean have guessed that he would attend prom, much less enjoy it as much as he was. Yet here he was, taking cheesy photos with his date and drinking punch that had yet to be spiked as miserable-looking chaperons like Mr. Henricksen watched from the sides.

The music had slowed down again, and they swayed together in a tight embrace. 

“Enjoying yourself?”

“In a strictly ironic and in no way ingenuous manner, obviously.” “Obviously,” Dean repeated seriously. 

Cas arched a brow. “What about you?” 

“Oh, this?” Dean asked in a mock-sincere voice, “The cheesy slow-dancing and all the balloons and streamers? Of course not, I’m not a _sucker,_ Cas.” His expression softened and his tone turned thoughtful. His heart swelled and he leaned in close, whispering next to Cas’ ear. “I can’t imagine being here with anyone else, Cas. It’s like we have this, I don’t know. Profound connection.” 

He didn’t dare pull back enough to get a read on Cas’ face, instead squeezing him tighter as they continued to dance. His chest was tight with the words he had refused to voice for days now, and against his better judgment he withdrew enough to look into Cas’ trusting eyes. Before he knew what he was saying, he blurted “Home.”

Cas tilted his head slightly, clearly confused. “What?” 

“That’s where I am when I disappear. I wasn’t in jail or desecrating graves or whatever the hell else goes around. My grandfather, Henry, he’s had a lot of health problems, and when he gets bad I stay home and take care of him. I'm trying to save up to get him the care he needs. He’s the only family I have left, and he needs me. End of story.”

Dean saw the question forming in Castiel’s eyes as he tilted his head, confused. “Is there a reason you’re telli—”

Cas was cut off by Brady rudely shoving past people in the crowd.

“Son of a _bitch_ ,” Dean muttered under his breath, right before Brady yanked him by the shoulder, pulling him off of Cas.

Brady roared, “Hey! What is Jess doing here with that loser nobody? I didn’t pay you to take out Castiel so that little punk could snake me!”

Dean froze, mouth gaping and eyes frantically looking back to Cas. Despite the loud music, everyone around them had gone stock still and was staring intently at the commotion. His eyes silently pleaded with Cas, desperate for a chance to explain, a chance to fix it. But it was futile; he saw Cas’ walls bricking up yet again.

“ _‘Profound connection_ ,’ huh?” Cas asked, huffing a humourless laugh before storming away. 

Dean pushed Brady off and took off after Cas, catching up to him at the top of the ballroom’s grand staircase. 

“Cas, just lis—” Dean pleaded.

Castiel rounded on him. “Listen? To you?” He jabbed him in the chest angrily and Dean winced. “How about you listen to me?You were fucking _paid_ to take me out by the one person in this world I truly hate.”

“Cas, it wasn’t like that, would you jus—”

“What was it like then?” Cas spat. “A down payment to get me to the prom, then a bonus for sleeping with me and bragging to everyone about it?” Cas’ typically deep voice turned shrill. “He’s resorted to _paying_ people to fuck with my life just because I wouldn’t put out three years ago? What kind of sick person goes along with that?” Hurt and anger warred on his face until he looked away, wiping at his eyes. 

Dean was struck dumb. His brain had screeched to a halt at the overload of information, and all he knew was that he didn’t have the words to charm or dance or sing his way out of this. 

Cas moved to leave, pausing momentarily. Fists clenched at his sides and his tone was low again. “Every bone in my body _screamed_ not to give you the time of day, and yet I decided to trust you, Dean.” He spoke his name like an epithet. “You’re not who I thought you were; you’re _exactly_ who I hoped you weren’t.” 

Cas reached into his suit pocket and flung the cassette tape Dean had given him onto the ground. 

“Cas, no.” Dean pleaded, his own voice coming out hoarse and barely intelligible. He knelt and plucked up the tape, holding it out. “It’s a gift, you keep those.”

Cas didn’t spare a single backward glance as he stormed out of the building. 

~~~~~~~

Sunday was a particularly lovely day, the Seattle cloud cover retreating temporarily to reveal blazing Spring sunshine. While the warblers chirped happily, celebrating the respite from the rain, Cas sat morosely on the porch swing, mindlessly stroking Leo and staring off into the street. No amount of blaring music had successfully drowned out the nightmarish words and images from prom. The porch door creaked open and Cas looked up to see his sister approach him with his favorite mug.

“You want?” She held the mug out towards him.

“Thanks.” He tried to smile, but the result was probably closer to a grimace. 

“So you sure you don’t want to come sailing with us? It’s a gorgeous day. It could take your mind off things.” 

He shook his head. “No, I’m fine.”

She reached over to scratch behind Leo’s ears. “I wanted to thank you for going the other night. I know that stuff is dumb to you but it really meant a lot to me.”

“I’m glad,” he said sincerely, this time managing a closed smile.

The tender moment ended as Sam jogged up the porch steps. He realized he’d interrupted a serious moment and paused awkwardly. Cas didn’t want or need the apology written in his eyes.

“Hey,” Sam said quietly to Jess.

She smiled at him. “Hi.”

“Ready to go?”

She nodded, then turned back to Cas and gave him a hug. “See you later. We’ll do something Cas-fun tonight, just us okay?”

Sam took her hand as they walked away and Cas sighed and looked back at Leo, who was blissfully sacked out and oblivious to all the crappy things in this world. The door opened again and Jody made her way towards the porch swing, taking the seat next to Leo. The dog lifted his head to glare at Jody for a moment before dropping back down.

“Where’s Jess off to?” she asked.

Cas cleared his throat, reverting automatically to his sarcastic tone. “She’s meeting up with some bikers, big ones.” 

“Funny.” Jody leaned back on the seat. “So, how was prom? Was it . . . _fly?_ ”

Cas snickered at Jody’s attempt at slang. “Parts of it.”

“Which parts?”

“Well, there was the part where Jess beat the living hell out of Tyson Brady,” he said nonchalantly. 

“Jess did _what_?”

He smirked. “Upset that I rubbed off on her?” Jody shook her head, clearly amused. “No, quite the opposite. I’m impressed. And glad she paid attention to what I taught her,” she paused and took a deep breath. “You know Castiel, you’ve been with me for so long that it’s been hard to admit you don’t need my help figuring things out anymore. Though she complains, Jess still lets me play a few innings. But you’ve had me on the bench for a while now. And when you go to Tufts, I won’t even be able to watch the game anymore.”

“ _When_ I go?” 

“Please don’t tell me you’ve changed your mind, I just put the check in the mail and—” 

Cas stared at her in disbelief. “No, no! I haven’t changed my mind.”

“Good.” Jody smiled back. “I know I’ve given you and Jess a hard time, but I just love both of you so much. I’ve never wanted anything bad to happen to either of you on my watch, and I wanted to keep you close as long as I could. I know that you can fend for yourself now, but I’ll never really stop worrying.” She looked at him with fond exasperation. “I also know I can’t protect you by keeping you on lockdown; you should be able to make your own choices.” 

Cas cut off her rambling by enveloping her in a big hug. Ignoring the tears that were forming, he whispered in her ear. “Thank you for everything you’ve given me.”

~~~~~

After prom, Dean was at a loss. He wanted Cas back, but he wasn’t sure he could come back from this. There were too many lies and hurt feelings. And he felt horrible that that’s what it had come to. He hadn’t been looking to find someone, he was fine alone, and then this whole thing with Cas had happened. So, he wallowed, though he would never admit it to anyone. 

He tried to distract himself. He looked over finances. And he couldn’t believe it, he’d finally saved enough. He made his way down the stairs, to find Henry in the living room watching _High Noon_. Dean took a seat on the sofa next to him. 

“Afternoon, Dean,” Henry smiled. 

“Hey,” Dean smiled back. “How’s the hip?” Henry shrugged. “Not as bad as getting shot was.” 

“Well I have some good news then. I’ve been putting some money aside for a while now, and I finally have enough to put you into a physical therapy program.” 

Henry frowned. “Dean, you shouldn’t be worrying about me. You should be saving for yourself, for your future.”

Dean waved dismissively. “I’ve put enough away for that. This is something for you.”

“Dean you really shouldn’t have—”

“But I did. I want to know you’ll be okay when I go away to college, I don’t want you hurting. You’ve given so much to me, I wanted to do something nice for you.”

Henry put his hand on Dean’s shoulder and squeezed. “Thank you, son.”

“Anything for you.”

“Everything okay with you lately?”

Dean hesitated. Henry was too perceptive to be satisfied with a lie. “Yeah school’s good. Uh, I kind of met someone.”

Henry’s face brightened. “So, who’s the lucky gal or fellow?” 

Dean rubbed his neck. “His name’s Castiel.”

“That name sounds familiar. I think I’ve seen him volunteering down at the senior center a few times, even went to the gala with Mildred. Seems like a good kid.”

“He’s great. But he’s pissed at me.”

Henry smiled. “Well I’m sure whatever happened you can both work it out. Tell him how you feel, apologize if you need to. Don’t give up on him.” 

“I don’t plan to. Thanks Henry.” 

“Anytime, son.” 

After his talk with Henry, Dean had a new game plan. No new diets, no marching bands. Brutal honesty. He sat at his desk and just started writing. 

_Cas,_

_Please don’t just crumple this up and throw it out, or burn it, or whatever other (perfectly justified) form of destruction I know you’re probably contemplating._

_Even I’m not stupid enough to think you’ll ever want to speak to me again, but you deserve to know the whole truth, so I’m going to tell you everything. I wish I had some Mr. Wickham to blame all of this on, but I’m no Mr. Darcy. First of all,_ _I’m sorry you had to find out about everything the way you did. I thought about coming clean so many times but it never seemed like the right time. What I mean is, I couldn’t imagine any way of telling you that didn’t end in you hating and leaving me forever, which was something I couldn’t bear. I’m sorry I was too selfish to give you the honesty you deserved from the beginning._

_Here’s something honest: I freaking hate Pansy Division. Christ, it sucks to admit that to you but they’re just loud racket to me. I’ll give them credit for their lyrics, though._

_Here’s something else: my brother Sam is a recovering addict. He left me with Dad when he got a scholarship to some fancy boarding school out east, and while he was there he got in over his head with this girl Ruby. He thought he was in love, but she got him hooked on all kinds of crap. He landed himself in the hospital and I bust my ass to get out there to help him, but he wouldn’t listen to me. Said he didn’t want to stop, that Ruby knew what she was doing, that he trusted her. Then my dad died and I moved in with gramps, and when Sam almost got expelled he finally started to see reason. He entered a rehab program all on his own and moved back here, but things have still been rocky with us. I was so angry with him for leaving me, for not letting me help him, but we’ve been trying to work things out. I’m not telling you this to feel sorry for me, but I thought you should know._

_Finally: Brady did pay me to go out with you so that he could date your sister. Something about your Mom’s dating rules, it didn’t seem important at the time. You should know that before that day, I would barely recognize you from English class. I had no idea Brady’s intentions weren’t purely centered around dating some chick, I really just did it for the money - money to help my grandfather, and to help Sam have a shot with a girl he really liked. Hell, it felt good taking money from someone that obnoxious. I wish I could tell you how sick I feel, knowing now what this must look like to you, what it looks like to me now that I know about Brady._

_You know my grandfather has a bad hip and I’ve been saving for years to get him into a good PT program. The extra cash finally put me in the black, and I didn’t want to jeopardize him getting the care he needed. At the time, it felt harmless to show some guy a good time._

_You were never supposed to find out, to get hurt like that._

_I was never supposed to fall for you._

_That was never part of the plan, but it happened. Even if the circumstances that lead us to go out in the first place were corrupt, the feelings weren’t, not on my end at least. As much as I regret ever getting mixed up with that douchebag, I can’t bring myself to regret growing closer to you. You are an incredible guy. I’m sorry._

_Dean_

He leaned back in his chair and read the letter over, swallowing thickly against the lump in his throat. He folded the paper and slid it into an envelope. Before he lost his courage, he grabbed his keys. He would drive over and slip the letter under Cas’ windshield wiper and hope for the best. In his case, that probably meant waking up with his balls intact and his car not set on-fire. He wouldn’t, _couldn’t_ dare let himself hope for more.

~~~~~~~

Cas fidgeted in his seat and chewed the end of his pencil as Mr. Henricksen cleared his throat.

“Alright, so I’m assuming everyone’s had time to complete their assignment. Except for Mr. Brady–” he clapped his palms together and started to laugh, unable to finish his statement as he looked over at Brady sulking at his desk behind a pair of sunglasses. “–who has an excuse. I knew you would get your ass kicked one day. Brady, lose the shades.”

Brady slowly removed his sunglasses, revealing a grotesque black eye and broken nose. The class joined in snickering along with Henricksen. 

Henricksen held a hand up, the laughter immediately tapering off. “Alright enough. Anyone brave enough to read theirs out loud?”

No one moved. Cas glanced around the room to see if anyone else would volunteer, anxiously avoiding Dean’s gaze. His presence tickled at the back of his neck, the sensation impossible to dismiss. He raised his hand. Might as well get this over with since he’d have to go one way or another.

“Lord, here we go,” Henricksen sighed, eyes raised heavenward. He motioned for him to come to the front of the room. 

Cas cleared his throat, and began.

_I hate the way you talk to me_

_And the way you cut your hair._

_I hate the way you drive my car_

_I hate it when you stare_

_I hate your big dumb Chevrolet_

_And the way you read my mind._

_I hate you so much it makes me sick_

_It even makes me rhyme._

He paused to take another deep breath, then continued.

_I hate the way you’re always right_

_I hate it when you lie._

_I hate it when you make me laugh_

_Even worse when you make me cry_

He blinked back the tears forming in his eyes and kept going.

_I hate it when you’re not around_

_And the fact that you didn’t call,_

_But mostly I hate the way I don’t hate you,_

_Not even close_

_Not even a little bit,_

_Not even at all._

As he finished, he looked directly at Dean, who looked just as miserable as him. Cas had never contacted him after finding the letter on his car, even though he’d read it at least twenty times. 

The class was stunned, completely silent. He fled for the exit, and didn’t look back.

~~~~~~~

Cas walked to his car after the day’s final bell. Today had been draining and he was ready to curl up with Leo and fall asleep with his book. He unlocked his car, surprised to see what appeared to be a wooden beehive taking up the passenger seat. He ran his fingers over the wood, tracing the intricately carved patterns. It was styled like a miniature house.

“Careful, that stain is still pretty fresh,” said a gruff voice behind him.

Cas tensed, then turned to face Dean. “Is this for me?” 

“Yeah, made it just for you.” Dean grabbed the back of his neck. “Thought you’d like it, be one step closer to saving the bees.”

Cas smiled. “Is that right?”

“It’s not every day you find a guy who looks sexy even when he’s crawling out of a fountain, minutes from hypothermia. Or who’ll puke on your new sneakers.”

Cas blushed and covered his face. “Oh God . . .”

Dean took this as a good sign, pressing forward and gently pulling his hands away from his face to kiss him, cradling Cas gently with his palms. 

Cas returned the kiss, then pulled back to chide, “You can’t just make me a beehive every time you screw up you know,” he teased. “Regardless of how many bees that would ultimately benefit.”

“Yeah, yeah, I know.” Dean smirked. “But there’s always Adirondack chairs,” he pressed a kiss to Cas’ jaw. “And dressers, and chest,” another kiss on his neck. Then, in a seductive whisper, “And maybe one day even a king size bed.” His lips traced along his ear.

“And don’t just think you can—” Cas tried again but was cut off by Dean finally pressing their lips together once again, this time slow and deep. Cas closed his eyes in surrender and wrapped his arms around Dean, smiling into the kiss. He could hold back his protests.

For now. 


	4. ACT IV

ACT IV

__ _2 months later_

Dean set the last of their things in the trunk and gently closed it, then walked over to where Cas was waiting and pecked him on the cheek. 

“Ready to go?” he asked.

Cas nodded. “I still think we should take my car,” he added stubbornly. 

“No way in hell, I won this right fair and _square_.”

Cas huffed, but got in the passenger seat and they set out onto the open road. 

“I thought maybe once we were gone I would feel some nostalgia, but it really _does_ feel good to be free of that hellhole,” he commented as they sped past the high school. Cas leaned out the window and flicked the building the bird for good measure. 

Dean smiled at his boyfriend. His _boyfriend._ The thought shot through him like an electric shock.

A few hours in, well clear of the city, Cas dialed down the volume and cleared his throat. “So, where exactly is this going?”

Dean frowned, pretending to check his map. “Well, unless I took the wrong exit we should be heading due south and hitting Vancouver pretty soo–”

“ _Dean_.”

Dean chuckled. Not that the guy would admit it under penalty of death, but Cas had been going crazy over Dean’s mysterious post-graduation plans. He had wanted to make sure everything was going to work out with Henry and his physical therapist and that Sam had gotten set up okay before making any big changes. Glancing over at the other boy, Dean was alarmed to see Cas looking genuinely nervous. 

Rather than cracking another joke, he confessed, “Well you’ll be at Tufts and I’ll be starting at MIT . . . so unless you’re already sick of me, I figured this was something we could keep going.”

Cas’ jaw dropped. 

“You’re going to MIT and you didn’t tell me?!” He shoved Dean and he winced, shying away from the blow. “You asshole! You knew for months now that I’d be at Tufts and you never said anything?” 

Dean looked away. “Well I didn’t want to say anything in case things didn’t work out with Gramps. Then, it just seemed like it’d be fun to surprise you.” 

Cas shook his head. “And here I was thinking we’d end up one of those couples who try doing long distance after they graduate,” Cas sighed dramatically. “Well, there goes my dream of fulfilling every high school rom-com cliché.”

Dean laced his fingers with Cas’. “Can’t get rid of me that easily, sweetheart.” 

Cas smiled back. “MIT? Seriously?”

Dean quirked an eyebrow. “You surprised?” 

“Not in _that_ way. You’re very smart. I’m more curious as to how admissions at MIT was willing to overlook so many absences.”

“Aww Cas, ye of little faith.” Dean shrugged. “MIT was apparently satisfied with my ninety-ninth percentile SAT scores and grades. It also helped that I rebuild engines in my spare time.” 

“MIT,” Cas repeated to himself under his breath. Louder, he said, “Well, I can’t wait to be in Boston with you. It’s a shame that Leo couldn’t come with us for this trip. I fear he likes you even more than me.”

Dean snorted. “No dogs allowed in Baby. Plus, I like that it’ll just be me, you, and the open road. And then the beach.” He grinned, dialing the volume back up and hitting the gas pedal.

Cas rolled his eyes. Dean worried that at this rate, they would get stuck like that one day. 

They took off towards California, Dean already mentally planning their next road trip.

To Boston. 

 


	5. ACT V

ACT V

_Present Day, November 2017_

Dean finds his husband looking down at his phone in front of the restaurant and greets him with a peck to the cheek.

“Hey sweetheart, sorry I was running a little late. I got caught up at the office.”

Cas smiles in return. “Don’t worry, I just arrived a moment ago. Shall we?” He holds out his arm and they enter the restaurant entwined.

During college, they had started a tradition, subsisting day to day on ramen and saving up all month to splurge on the trendiest and fanciest meals in town. Now that they had steadier incomes, the tradition had only flourished. Tonight’s restaurant, Harvest Beat, is dimly lit, candles burning on every table and fittingly enough serves fancy vegan and vegetarian fare.

“Vegan joints have come a long way since our first date, huh Cas?” Dean points out to his husband, remembering what almost could have been a disaster of a first date.

Cas laughs as he shrugs off his trenchcoat, an item he had picked up and grown attached to at a thrift shop on a road trip a few years back. It was a far cry from the grunge look Cas had been aiming for when they first met, but Dean still gave him grief about it resembling a flasher coat.

Dean smiles as he thinks of his husband of ten years. He ran his thumb along the wooden ring he’d fashioned for them senior year of college. He’d carried the matching set of rings around for another three years before he’d been able to find the courage to ask Cas to marry him. They’d had their ups and downs like any couple, but always came out stronger. Cas is the love of his life, and he’s ready to take the next step in their journey together.

He tries to focus as Cas chatters excitedly about their upcoming Thanksgiving plans. Sam and Jess would be coming with their kids to Dean and Cas’ house, along with Jody. Charlie would also be flying up from California to join them, assuming she managed to step away from the tech empire she had built from the ground up.

“So, I’ve been thinking,” Dean clears his throat. This was it. “I love you, and I want to have everything with you. We have the house, the dog, the white picket fence, and I think we might be ready to add a kid into the mix.”

Cas’ eyes brighten, but he waits for Dean to finish.

“But given how we both grew up, and just how the world is already an overpopulated mess, I was thinking that we could maybe adopt an older kid. . . someone who really needs a home and a support system.”

He looks up to see Cas beaming at him. Almost as happy as he’d looked when Dean proposed. “I’ve been thinking the same thing too.”

“So we’re gonna take in some surly teenagers, then?”

“At least grunge is finally dead. I don’t know if you could handle a baby. They cry all the time, and the parents never get to sleep. That just wouldn’t work in our household.” Cas jokes. “You’re an angry sleeper, like a bear.”

He snorts. He liked his beauty sleep, and didn’t like it being disturbed. He wasn’t ashamed of that, but he’d play along. “Shut up, I’m great with babies! But you forget now there are _hipsters,_ ” Dean says as he eyes some of the other restaurant patrons warily.

Cas smiles and takes Dean’s hand into his across the table. “Of course you are, honey. Whatever happens though, I know we can handle it.”

~~~~~~

Four months later, Dean and Cas welcome Jack Kline into their home and lives.

 

_FIN_

**Author's Note:**

> Thank you for reading! We hope you all enjoyed this fic as much as we enjoyed writing it!  
> You can find us on tumblr as vulcancas and preciousmish if you wanna come chat with us xoxo
> 
> (btw in case you guys are curious homo-a-go-go is most definitely a real event, we just used some creative license to have it fit our location needs ;) )


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